Production Method 1

18162-48-6

86120-46-9

Reaction Conditions

1.1 Reagents: Imidazole Solvents: Tetrahydrofuran ;  3 h, rt

Reference

Development of Intravascular Contrast Agents for MRI Using Gadolinium Chelates

Kittigowittana, Krisada; et al, ChemMedChem, 2011, 6(5), 781-787

Production Method 2

76782-82-6

86120-46-9

Reaction Conditions

1.1 Reagents: Butyllithium ,  N,N,N′,N′-Tetramethylethylenediamine Solvents: Tetrahydrofuran ;  30 min, -78 °C; 1.5 h, rt

Reference

Reactivity pattern of bis(propargyloxy)disulfides: tandem rearrangements and cyclizations

Braverman, Samuel; et al, Synthesis, 2011, (11), 1741-1750

Production Method 3

76782-82-6

86120-46-9

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane ;  -78 °C; 30 min, -78 °C
1.2 -78 °C; overnight, -78 °C → rt
1.3 Reagents: Water ;  0 °C

Reference

Influence of the Acetylenic Substituent on the Intramolecular Carbolithiation of Alkynes

Girard, Anne-Lise; et al, European Journal of Organic Chemistry, 2012, 2012(15), 2895-2905

Production Method 4

86120-46-9

Reaction Conditions

1.1 Reagents: Methanol Catalysts: Silica Solvents: Methanol ;  4 h, rt

Reference

Deprotection of a silyl group with mesoporous silica

Itoh, Akichika; et al, Chemical & Pharmaceutical Bulletin, 2007, 55(6), 861-864

Production Method 5

537684-35-8

537684-34-7

86120-46-9

537684-36-9

91202-69-6

Reaction Conditions

1.1 Reagents: Iodine Solvents: Diethyl ether
2.1 Reagents: Methyllithium ;  15 min, -30 °C
2.2 Reagents: tert-Butyllithium ;  90 min, -90 °C
2.3 2 h, -90 °C

Reference

On the construction of 2-substituted 1,4-diacetoxybutadiene moiety: application to the synthesis of (±)-caulerpenyne

Commeiras, Laurent; et al, Tetrahedron Letters, 2003, 44(11), 2311-2314

Production Method 6

18162-48-6

145350-62-5

86120-46-9

537684-36-9

91202-69-6

Reaction Conditions

1.1 Reagents: Imidazole Solvents: Dimethylformamide
2.1 Reagents: Iodine Solvents: Diethyl ether
3.1 Reagents: Methyllithium ;  15 min, -30 °C
3.2 Reagents: tert-Butyllithium ;  90 min, -90 °C
3.3 2 h, -90 °C

Reference

On the construction of 2-substituted 1,4-diacetoxybutadiene moiety: application to the synthesis of (±)-caulerpenyne

Commeiras, Laurent; et al, Tetrahedron Letters, 2003, 44(11), 2311-2314

Production Method 7

86120-46-9

537684-36-9

91202-69-6

Reaction Conditions

1.1 Reagents: Azobisisobutyronitrile Solvents: Benzene ;  reflux
2.1 Reagents: Imidazole Solvents: Dimethylformamide
3.1 Reagents: Iodine Solvents: Diethyl ether
4.1 Reagents: Methyllithium ;  15 min, -30 °C
4.2 Reagents: tert-Butyllithium ;  90 min, -90 °C
4.3 2 h, -90 °C

Reference

On the construction of 2-substituted 1,4-diacetoxybutadiene moiety: application to the synthesis of (±)-caulerpenyne

Commeiras, Laurent; et al, Tetrahedron Letters, 2003, 44(11), 2311-2314

Production Method 8

18162-48-6

86120-46-9

Reaction Conditions

1.1 Reagents: Imidazole Solvents: Tetrahydrofuran ;  15 min, 0 °C; 0 °C → rt

Reference

Function-Oriented and Modular (+/-)-cis-Pseudoguaianolide Synthesis: Discovery of New Nrf2 Activators and NF-κB Inhibitors

Emmetiere, Fabien; et al, Chemistry - A European Journal, 2021, 27(17), 5564-5571

Production Method 9

18162-48-6

86120-46-9

Reaction Conditions

1.1 Reagents: Imidazole Solvents: Tetrahydrofuran

Reference

Viridiofungins and xeniolide F: target oriented synthesis using different rearrangement reactions of a common substrate class

Pollex, Annett, 2006, , ,

Production Method 10

76782-82-6

86120-46-9

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane ;  -78 °C; -78 °C → 0 °C; 1 h, 0 °C; 0 °C → -78 °C
1.2 -78 °C → rt; 16 h, rt
1.3 Reagents: Ammonium chloride Solvents: Water

Reference

Rhodium-Catalyzed Hydroformylation of 1,1-Disubstituted Allenes Employing the Self-Assembling 6-DPPon System

Koepfer, Alexander; et al, Angewandte Chemie, 2015, 54(23), 6913-6917

Production Method 11

18162-48-6

86120-46-9

Reaction Conditions

1.1 Reagents: Imidazole ,  4-(Dimethylamino)pyridine Solvents: Dimethylformamide
2.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane ;  -78 °C; -78 °C → 0 °C; 1 h, 0 °C; 0 °C → -78 °C
2.2 -78 °C → rt; 16 h, rt
2.3 Reagents: Ammonium chloride Solvents: Water

Reference

Rhodium-Catalyzed Hydroformylation of 1,1-Disubstituted Allenes Employing the Self-Assembling 6-DPPon System

Koepfer, Alexander; et al, Angewandte Chemie, 2015, 54(23), 6913-6917

Production Method 12

18162-48-6

86120-46-9

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Dichloromethane ;  2 h, rt
2.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane ;  -78 °C; 30 min, -78 °C
2.2 -78 °C; overnight, -78 °C → rt
2.3 Reagents: Water ;  0 °C

Reference

Influence of the Acetylenic Substituent on the Intramolecular Carbolithiation of Alkynes

Girard, Anne-Lise; et al, European Journal of Organic Chemistry, 2012, 2012(15), 2895-2905

Production Method 13

86120-46-9

Reaction Conditions

1.1 Solvents: Methanol

Reference

Selective deprotection of triethylsilyl group in the presence of tert-butyldimethylsilyl group with MCM-41/MeOH heterogeneous system

Itoh, Akichika; et al, Synlett, 1999, (3), 357-359

Production Method 14

994-30-9

86120-46-9

86120-46-9

Reaction Conditions

1.1 Reagents: Imidazole Solvents: Dimethylformamide ;  rt; overnight, rt
2.1 Reagents: Methanol Catalysts: Silica Solvents: Methanol ;  4 h, rt

Reference

Deprotection of a silyl group with mesoporous silica

Itoh, Akichika; et al, Chemical & Pharmaceutical Bulletin, 2007, 55(6), 861-864

Production Method 15

179949-75-8

264125-54-4

86120-46-9

537684-36-9

91202-69-6

Reaction Conditions

1.1 Reagents: Methyllithium ;  15 min, -30 °C
1.2 Reagents: tert-Butyllithium ;  90 min, -90 °C
1.3 2 h, -90 °C

Reference

On the construction of 2-substituted 1,4-diacetoxybutadiene moiety: application to the synthesis of (±)-caulerpenyne

Commeiras, Laurent; et al, Tetrahedron Letters, 2003, 44(11), 2311-2314

4-(tert-butyldimethylsilyl)oxybut-2-yn-1-ol Raw materials

• tert-butyl(chloro)dimethylsilane
• 2-Buten-1-ol, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-(tributylstannyl)-, (2Z)-
• 2-Buten-1-ol, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-(tributylstannyl)-, (2Z)-
• Chlorotriethylsilane
• 2-Butene-1,4-diol, 2-(tributylstannyl)-, (2Z)-
• 4-{[tert-Butyl(dimethyl)silyl]oxy}-3-iodobut-2-en-1-ol
• 4-(tert-butyldimethylsilyl)oxybut-2-yn-1-ol
• 3-(tert-Butyldimethylsilyloxy)-1-propyne
• 2-Buten-1-ol, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-iodo-, (2Z)-

4-(tert-butyldimethylsilyl)oxybut-2-yn-1-ol Preparation Products

• 1,3-Pentanediol, 2-[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethylidene]-, (2Z)- (537684-36-9)
• 4-(tert-butyldimethylsilyl)oxybut-2-yn-1-ol (86120-46-9)
• 2-Buten-1-ol, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, (2E)- (91202-69-6)

• 1. Excitation dependent recombination studies on SnO2/TiO2 electrospun nanofibers?
  Veluru Jagadeesh babu,Sesha Vempati RSC Adv., 2015,5, 66367-66375
• 2. Embedding heteroatoms: an effective approach to create porphyrin-based functional materials
  Norihito Fukui,Keisuke Fujimoto,Hideki Yorimitsu,Atsuhiro Osuka Dalton Trans., 2017,46, 13322-13341
• 3. Excitable dynamics in the bromate–sulfite–ferrocyanide reaction
  J. Zagora,M. Vosla?,L. Schreiberová,I. Schreiber Phys. Chem. Chem. Phys., 2002,4, 1284-1291
• 4. Fe3O4 nanosphere@microporous organic networks: enhanced anode performances in lithium ion batteries through carbonization?
  Byungho Lim,Jaewon Jin,Jin Yoo,Seung Yong Han,Kyeongyeol Kim,Sungah Kang,Nojin Park,Sang Moon Lee,Hae Jin Kim,Seung Uk Son Chem. Commun., 2014,50, 7723-7726
• 5. Excellent lithium ion storage property of porous MnCo2O4 nanorods?
  Peiyuan Zeng,Xiaoxiao Wang,Ming Ye,Qiuyang Ma,Jianwen Li,Wanwan Wang,Baoyou Geng,Zhen Fang RSC Adv., 2016,6, 23074-23084

• 133910-89-1(3-Pentyn-2-ol, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, (2S)-)
• 165404-59-1(2,4-Hexadiyn-1-ol, 6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-)
• 75859-97-1(4-(tert-butyldimethylsilyl)oxybut-2-ynal)
• 163591-85-3(4,9-Dioxa-3,10-disiladodec-6-yne, 2,2,3,3,10,10,11,11-octamethyl-)
• 110796-98-0((4-bromobut-2-yn-1-yl)oxy(tert-butyl)dimethylsilane)
• 76782-82-6(3-(tert-Butyldimethylsilyloxy)-1-propyne)
• 91509-32-9(Lithium, [3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-propynyl]-)
• 111999-90-7(tert-butyl-dimethyl-(4-trimethylsilylbut-2-ynoxy)silane)
• 214978-04-8(3-Pentyn-2-ol, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-)
• 83591-03-1(Silane, (2-butynyloxy)(1,1-dimethylethyl)dimethyl-)