- Divergent Total Synthesis of Triptolide, Triptonide, Tripdiolide, 16-Hydroxytriptolide, and Their AnaloguesBy Xu, Hongtao et al, Journal of Organic Chemistry, 2014, 79(21), 10110-10122
Cas no 139713-80-7 (16-Hydroxytriptolide)
16-Hydroxytriptolide structure
Product Name:16-Hydroxytriptolide
CAS No:139713-80-7
MF:C20H24O7
MW:376.400366783142
CID:64608
PubChem ID:126556
Update Time:2025-04-18
16-Hydroxytriptolide Chemical and Physical Properties
Names and Identifiers
-
- 16-Hydroxytriptolide
- 16 Hydroxytriptolide
- (3bS,4aS,5aS,6R,6aR,7aS,7bS,8aS,8bS)-6-hydroxy-6a-[(2S)-1-hydroxypropan-2-yl]-8b-methyl-3b,4,4a,6,6a,7a,7b,8b,9,10-decahydrotrisoxireno[6,7:8a,9:4b,5]phenanthro[1,2-c]furan-1(3H)-one
- Triptolide, 16-hydroxy-, (15S)-
- Triptolide,16-hydroxy-, (15S)-
- (15S)-16-Hydroxytriptolide
- 16-Hydroxytryptolide
- Trisoxireno[4b,5:6,7:8a,9]phenanthro[1,2-c]furan-1(3H)-one,3b,4,4a,6,6a,7a,7b,8b,9,10-decahydro-6-hydroxy-6a-(2-hydroxy-1-methylethyl)-,[3bS-[3ba,4aa,5aR*,6b,6ab(R*),7ab,7ba,8aR*,8ba]]-
- CHEBI:132621
- DTXSID70930562
- (1S,2S,4S,5S,7R,8R,9S,11S,13S)-8-hydroxy-7-[(2S)-1-hydroxypropan-2-yl]-1-methyl-3,6,10,16-tetraoxaheptacyclo[11.7.0.02,4.02,9.05,7.09,11.014,18]icos-14(18)-en-17-one
- 139713-80-7
-
- Inchi： 1S/C20H24O7/c1-8(6-21)18-13(26-18)14-20(27-14)17(2)4-3-9-10(7-24-15(9)22)11(17)5-12-19(20,25-12)16(18)23/h8,11-14,16,21,23H,3-7H2,1-2H3/t8-,11-,12-,13-,14-,16+,17-,18-,19+,20+/m0/s1
- InChI Key： HPTCYMNPHWXVLA-UBBHAYRHSA-N
- SMILES： O1[C@H]2[C@H]3[C@@]([C@@H](C)CO)([C@H]([C@]45[C@H](C[C@H]6C7COC(C=7CC[C@]6(C)[C@@]142)=O)O5)O)O3
Computed Properties
- Exact Mass: 376.152
- Monoisotopic Mass: 376.152
- Isotope Atom Count: 0
- Hydrogen Bond Donor Count: 2
- Hydrogen Bond Acceptor Count: 7
- Heavy Atom Count: 27
- Rotatable Bond Count: 2
- Complexity: 838
- Covalently-Bonded Unit Count: 1
- Defined Atom Stereocenter Count: 10
- Undefined Atom Stereocenter Count : 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Surface Charge: 0
- Tautomer Count: nothing
- XLogP3: -1
- Topological Polar Surface Area: 104A^2
Experimental Properties
- Density: 1.56
- Boiling Point: 659.7°Cat760mmHg
- Flash Point: 241.8°C
- Refractive Index: 1.67
- PSA: 104.35000
- LogP: 0.07550
16-Hydroxytriptolide Pricemore >>
| Related Categories | No. | Product Name | Cas No. | Purity | Specification | Price | update time | Inquiry |
|---|---|---|---|---|---|---|---|---|
| TRC | H960005-500?g |
16-Hydroxytriptolide |
139713-80-7 | 500?g |
550.00 | 2021-08-04 | ||
| TRC | H960005-1mg |
16-Hydroxytriptolide |
139713-80-7 | 1mg |
$1275.00 | 2023-05-18 | ||
| TRC | H960005-2.5mg |
16-Hydroxytriptolide |
139713-80-7 | 2.5mg |
$3077.00 | 2023-05-18 | ||
| TRC | H960005-500μg |
16-Hydroxytriptolide |
139713-80-7 | 500μg |
$ 570.00 | 2022-06-04 | ||
| TRC | H960005-.5mg |
16-Hydroxytriptolide |
139713-80-7 | 5mg |
$655.00 | 2023-05-18 |
16-Hydroxytriptolide Production Method
Production Method 1
Reaction Conditions
1.1R:H2, C:Pd, S:MeOH, 8 h, rt
1.2R:Diimidazolyl ketone, R:MeNHOMe-HCl, S:CH2Cl2, 3 h, rt
1.3S:THF, 0°C; 0°C → 23°C; 3 h, 23°C
2.1R:CeCl3 ?7H2O, S:MeOH, 15 min, -5°C
2.2R:NaBH4, 30 min, -5°C
2.3R:HCl, S:H2O
2.4S:EtCO2H, 24 h, reflux
3.1R:LiOH, S:H2O, S:MeOH, 3 h, rt
3.2R:Diimidazolyl ketone, S:CH2Cl2, 3 h, rt
4.1R:BuLi, S:THF, 30 min, -78°C; -78°C → -20°C; -20°C → -78°C
4.2S:THF, -78°C; 1 h, -78°C → -20°C; -20°C → -40°C
4.3R:H2O, -40°C, pH 7
5.1R:Et3N, R:HCO2H, C:195516-84-8, S:THF, 2.5 h, rt
6.1R:K2CO3, S:MeOH, 2.5 h, rt
6.2R:1H-Imidazole, S:DMF, 0°C; overnight, rt
7.1C:13465-09-3, S:CH2Cl2, 30 min, -20°C
7.2S:CH2Cl2, 4 h, -20°C
7.3R:NaHCO3, S:H2O
8.1R:BH3-THF, S:THF, 0°C; 4 h, rt; rt → 0°C
8.2R:NaOH, R:H2O2, S:H2O, 0°C; 3 h, rt
8.3R:Na2S2O3, S:H2O
9.1R:Bu4N+ ?I-, R:NaH, S:DMF, 0°C; 30 min, rt
9.2overnight, rt
9.3R:p-MeC6H4SO3H, S:MeOH, 3 h, rt
10.1R:H2SO4, R:CrO3, S:H2O, S:Me2CO, 20 min, 0°C
10.2R:Me2CHOH
10.3R:K [N(SiMe3)2], S:THF, S:PhMe, 30 min, -78°C
10.4S:THF, -78°C; 30 min, -78°C; overnight, -78°C → rt
11.1R:DDQ, S:H2O, S:CH2Cl2, 0.5 h, rt
11.2R:Na2S2O3, S:H2O
11.3R:LiCl, R:Bu3N, C:Pd(PPh3)4, S:MeCN, 8 h, rt
12.1C:Et3SiH, C:RhCl(PPh3)3, S:PhMe, rt; 8 h, reflux
13.1R:Ce(NH4)2(NO3)6, S:H2O, S:MeCN, 1.5 h, rt
13.2R:H2SO4, R:CrO3, S:H2O, S:Me2CO, 30 min, 0°C
13.3R:Me2CHOH
14.1R:BBr3, S:CH2Cl2, 1 h, -78°C
15.1R:NaH, S:DMF, 0°C; 30 min, rt
15.22 h, rt
16.1R:PhNMe2, 8 h, reflux
17.1R:NaHCO3, R:NaIO4, C:OsO4, S:H2O, S:t-BuOH, 12 h, rt
17.2R:Na2S2O3, S:H2O, 30 min, rt
18.1R:NaBH4, R:NH4Cl, S:H2O, S:MeOH, 30 min, 0°C
18.2R:NaIO4, S:H2O, S:MeOH, 50 min, 0°C
19.1R:Na2 EDTA, R:MeC(=O)CF3, R:NaHCO3, R:Oxone, S:H2O, S:MeCN, 5 h, 0°C
19.2R:K2CO3, R:H2O2, S:H2O, S:MeOH, 2 h, 0°C
20.1R:NaBH4, S:MeOH, 1 h, 0°C
20.2R:NH4Cl, S:H2O
Show MoreShow Less
1.2R:Diimidazolyl ketone, R:MeNHOMe-HCl, S:CH2Cl2, 3 h, rt
1.3S:THF, 0°C; 0°C → 23°C; 3 h, 23°C
2.1R:CeCl3 ?7H2O, S:MeOH, 15 min, -5°C
2.2R:NaBH4, 30 min, -5°C
2.3R:HCl, S:H2O
2.4S:EtCO2H, 24 h, reflux
3.1R:LiOH, S:H2O, S:MeOH, 3 h, rt
3.2R:Diimidazolyl ketone, S:CH2Cl2, 3 h, rt
4.1R:BuLi, S:THF, 30 min, -78°C; -78°C → -20°C; -20°C → -78°C
4.2S:THF, -78°C; 1 h, -78°C → -20°C; -20°C → -40°C
4.3R:H2O, -40°C, pH 7
5.1R:Et3N, R:HCO2H, C:195516-84-8, S:THF, 2.5 h, rt
6.1R:K2CO3, S:MeOH, 2.5 h, rt
6.2R:1H-Imidazole, S:DMF, 0°C; overnight, rt
7.1C:13465-09-3, S:CH2Cl2, 30 min, -20°C
7.2S:CH2Cl2, 4 h, -20°C
7.3R:NaHCO3, S:H2O
8.1R:BH3-THF, S:THF, 0°C; 4 h, rt; rt → 0°C
8.2R:NaOH, R:H2O2, S:H2O, 0°C; 3 h, rt
8.3R:Na2S2O3, S:H2O
9.1R:Bu4N+ ?I-, R:NaH, S:DMF, 0°C; 30 min, rt
9.2overnight, rt
9.3R:p-MeC6H4SO3H, S:MeOH, 3 h, rt
10.1R:H2SO4, R:CrO3, S:H2O, S:Me2CO, 20 min, 0°C
10.2R:Me2CHOH
10.3R:K [N(SiMe3)2], S:THF, S:PhMe, 30 min, -78°C
10.4S:THF, -78°C; 30 min, -78°C; overnight, -78°C → rt
11.1R:DDQ, S:H2O, S:CH2Cl2, 0.5 h, rt
11.2R:Na2S2O3, S:H2O
11.3R:LiCl, R:Bu3N, C:Pd(PPh3)4, S:MeCN, 8 h, rt
12.1C:Et3SiH, C:RhCl(PPh3)3, S:PhMe, rt; 8 h, reflux
13.1R:Ce(NH4)2(NO3)6, S:H2O, S:MeCN, 1.5 h, rt
13.2R:H2SO4, R:CrO3, S:H2O, S:Me2CO, 30 min, 0°C
13.3R:Me2CHOH
14.1R:BBr3, S:CH2Cl2, 1 h, -78°C
15.1R:NaH, S:DMF, 0°C; 30 min, rt
15.22 h, rt
16.1R:PhNMe2, 8 h, reflux
17.1R:NaHCO3, R:NaIO4, C:OsO4, S:H2O, S:t-BuOH, 12 h, rt
17.2R:Na2S2O3, S:H2O, 30 min, rt
18.1R:NaBH4, R:NH4Cl, S:H2O, S:MeOH, 30 min, 0°C
18.2R:NaIO4, S:H2O, S:MeOH, 50 min, 0°C
19.1R:Na2 EDTA, R:MeC(=O)CF3, R:NaHCO3, R:Oxone, S:H2O, S:MeCN, 5 h, 0°C
19.2R:K2CO3, R:H2O2, S:H2O, S:MeOH, 2 h, 0°C
20.1R:NaBH4, S:MeOH, 1 h, 0°C
20.2R:NH4Cl, S:H2O
Show MoreShow Less
Reference
16-Hydroxytriptolide Raw materials
- 4-Methoxybenzylchloride
- tert-butyl(chloro)dimethylsilane
- Bromo(isopropenyl)magnesium Solution (0.5M in THF)
- (E)-3-(2-methoxyphenyl)prop-2-enoic acid
- Triethyl orthoacetate
- N,N-Bis(trifluoromethylsulfonyl)aniline
- ethynyltrimethylsilane
- N,O-Dimethylhydroxylamine hydrochloride
- trans-Crotyl bromide
16-Hydroxytriptolide Preparation Products
16-Hydroxytriptolide Related Literature
-
Zhao-Li Zhou,Ya-Xi Yang,Jian Ding,Yuan-Chao Li,Ze-Hong Miao Nat. Prod. Rep. 2012 29 457
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