(7E,9E)-(2S,3aR,5R,6S,11R,12R,16R,17S,17aS)-12-Ethyl-6,16-dihydroxy-2-methoxy-5,9,17-trimethyl-11-trityloxymethyl-2,3,3a,4,5,6,11,12,15,16,17,17a-dodecahydro-1,13-dioxa-cyclopentacyclohexadecen-14-one

Base Information

• Chemical Name: (7E,9E)-(2S,3aR,5R,6S,11R,12R,16R,17S,17aS)-12-Ethyl-6,16-dihydroxy-2-methoxy-5,9,17-trimethyl-11-trityloxymethyl-2,3,3a,4,5,6,11,12,15,16,17,17a-dodecahydro-1,13-dioxa-cyclopentacyclohexadecen-14-one
• CAS No.: 84710-26-9
• Molecular Formula: C₄₃H₅₄O₇
• Molecular Weight: 682.898
• Mol file: 84710-26-9.mol

Synonyms:(7E,9E)-(2S,3aR,5R,6S,11R,12R,16R,17S,17aS)-12-Ethyl-6,16-dihydroxy-2-methoxy-5,9,17-trimethyl-11-trityloxymethyl-2,3,3a,4,5,6,11,12,15,16,17,17a-dodecahydro-1,13-dioxa-cyclopentacyclohexadecen-14-one

Chemical Property of (7E,9E)-(2S,3aR,5R,6S,11R,12R,16R,17S,17aS)-12-Ethyl-6,16-dihydroxy-2-methoxy-5,9,17-trimethyl-11-trityloxymethyl-2,3,3a,4,5,6,11,12,15,16,17,17a-dodecahydro-1,13-dioxa-cyclopentacyclohexadecen-14-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (7E,9E)-(2S,3aR,5R,6S,11R,12R,16R,17S,17aS)-12-Ethyl-6,16-dihydroxy-2-methoxy-5,9,17-trimethyl-11-trityloxymethyl-2,3,3a,4,5,6,11,12,15,16,17,17a-dodecahydro-1,13-dioxa-cyclopentacyclohexadecen-14-one

There total 64 articles about (7E,9E)-(2S,3aR,5R,6S,11R,12R,16R,17S,17aS)-12-Ethyl-6,16-dihydroxy-2-methoxy-5,9,17-trimethyl-11-trityloxymethyl-2,3,3a,4,5,6,11,12,15,16,17,17a-dodecahydro-1,13-dioxa-cyclopentacyclohexadecen-14-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

20-O-Methyl-23-O-trityltylonolide Hemiacetal (81132-63-0) → (7E,9E)-(2S,3aR,5R,6S,11R,12R,16R,17S,17aS)-12-Ethyl-6,16-dihydroxy-2-methoxy-5,9,17-trimethyl-11-trityloxymethyl-2,3,3a,4,5,6,11,12,15,16,17,17a-dodecahydro-1,13-dioxa-cyclopentacyclohexadecen-14-one (84710-26-9)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In methanol; at -78 ℃; for 0.25h;

DOI:10.1021/jo00154a033

Reference yield:

(5R,6S)-5-(2-Benzyloxy-ethyl)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-tetrahydro-pyran-2-one (83061-04-5) → (7E,9E)-(2S,3aR,5R,6S,11R,12R,16R,17S,17aS)-12-Ethyl-6,16-dihydroxy-2-methoxy-5,9,17-trimethyl-11-trityloxymethyl-2,3,3a,4,5,6,11,12,15,16,17,17a-dodecahydro-1,13-dioxa-cyclopentacyclohexadecen-14-one (84710-26-9)

Guidance literature:

Multi-step reaction with 15 steps

1: LDA / tetrahydrofuran / -78 deg C -> -40 deg C

2: hydrogen / Pd-C / ethanol

3: CrO₃*2Py / CH₂Cl₂

4: TsOH

5: 95 percent / LiAlH₄ / diethyl ether / 0 °C

6: 95 percent / CrO₃*2Py / CH₂Cl₂ / 1 h / 0 °C

8: LiAlH₄ / tetrahydrofuran / 5 °C

9: DMAP, Py

11: 1.) CrO₃*2Py / 1.) 0 deg C, 2.) THF, -78 deg C, 10 min

12: sodium methoxide / methanol

13: 1 N NaOH / methanol / 2 h / 60 °C

14: triphenylphosphine / tetrahydrofuran

15: toluene / 24 h / Heating

With pyridine; dmap; sodium hydroxide; lithium aluminium tetrahydride; hydrogen; sodium methylate; dipyridine chromium trioxide; toluene-4-sulfonic acid; triphenylphosphine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; toluene;

DOI:10.1021/ja00385a038

Reference yield:

(5R,6S)-5-(2-Benzyloxy-ethyl)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-3-methyl-tetrahydro-pyran-2-one → (7E,9E)-(2S,3aR,5R,6S,11R,12R,16R,17S,17aS)-12-Ethyl-6,16-dihydroxy-2-methoxy-5,9,17-trimethyl-11-trityloxymethyl-2,3,3a,4,5,6,11,12,15,16,17,17a-dodecahydro-1,13-dioxa-cyclopentacyclohexadecen-14-one (84710-26-9)

Guidance literature:

Multi-step reaction with 14 steps

1: hydrogen / Pd-C / ethanol

2: CrO₃*2Py / CH₂Cl₂

3: TsOH

4: 95 percent / LiAlH₄ / diethyl ether / 0 °C

5: 95 percent / CrO₃*2Py / CH₂Cl₂ / 1 h / 0 °C

7: LiAlH₄ / tetrahydrofuran / 5 °C

8: DMAP, Py

10: 1.) CrO₃*2Py / 1.) 0 deg C, 2.) THF, -78 deg C, 10 min

11: sodium methoxide / methanol

12: 1 N NaOH / methanol / 2 h / 60 °C

13: triphenylphosphine / tetrahydrofuran

14: toluene / 24 h / Heating

With pyridine; dmap; sodium hydroxide; lithium aluminium tetrahydride; hydrogen; sodium methylate; dipyridine chromium trioxide; toluene-4-sulfonic acid; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; toluene;

DOI:10.1021/ja00385a038

upstream raw materials:

(3R,4S)-4-[(2S,3R)-3-((4E,6E)-(2R,8R,9S)-3,9-Dihydroxy-2,6-dimethyl-8-trityloxymethyl-undeca-4,6-dienyl)-5-methoxy-tetrahydro-furan-2-yl]-3-hydroxy-pentanethioic acid S-pyridin-2-yl ester

(7E,9E)-(3aR,5R,11R,12R,16R,17S,17aS)-12-Ethyl-16-hydroxy-2-methoxy-5,9,17-trimethyl-11-trityloxymethyl-3,3a,4,5,11,12,15,16,17,17a-decahydro-2H-1,13-dioxa-cyclopentacyclohexadecene-6,14-dione

3,5-Didesoxy-1,2-O-isopropyliden-3-C-methyl-α-D-xylo-hexofuranose

(3R,4S,5R)-5-Ethyl-3-hydroxy-4-hydroxymethyl-dihydro-furan-2-one

Downstream raw materials:

(3R,4S)-4-[(2S,3R)-3-((4E,6E)-(2R,8R,9S)-3,9-Dihydroxy-2,6-dimethyl-8-trityloxymethyl-undeca-4,6-dienyl)-5-methoxy-tetrahydro-furan-2-yl]-3-hydroxy-pentanoic acid

(7E,9E)-(3aR,5R,11R,12R,16R,17S,17aS)-12-Ethyl-16-hydroxy-2-methoxy-5,9,17-trimethyl-11-trityloxymethyl-3,3a,4,5,11,12,15,16,17,17a-decahydro-2H-1,13-dioxa-cyclopentacyclohexadecene-6,14-dione

(3R,4S)-4-[(2S,3R)-3-((4E,6E)-(2R,8R,9S)-3,9-Dihydroxy-2,6-dimethyl-8-trityloxymethyl-undeca-4,6-dienyl)-5-methoxy-tetrahydro-furan-2-yl]-3-hydroxy-pentanethioic acid S-pyridin-2-yl ester

(3R,4S)-4-[(2S,3R)-3-((4E,6E)-(2R,8R,9S)-3,9-Dihydroxy-2,6-dimethyl-8-trityloxymethyl-undeca-4,6-dienyl)-5-methoxy-tetrahydro-furan-2-yl]-3-hydroxy-pentanoic acid methyl ester