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

Base Information

• Chemical Name: (3R,4S)-4-[(2S,3R,5S)-3-((4E,6E)-(2R,3S,8R,9R)-3,9-Dihydroxy-2,6-dimethyl-8-trityloxymethyl-undeca-4,6-dienyl)-5-methoxy-tetrahydro-furan-2-yl]-3-hydroxy-pentanoic acid methyl ester
• CAS No.: 83114-35-6
• Molecular Formula: C₄₄H₅₈O₈
• Molecular Weight: 714.94
• Mol file: 83114-35-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 69 articles about (3R,4S)-4-[(2S,3R,5S)-3-((4E,6E)-(2R,3S,8R,9R)-3,9-Dihydroxy-2,6-dimethyl-8-trityloxymethyl-undeca-4,6-dienyl)-5-methoxy-tetrahydro-furan-2-yl]-3-hydroxy-pentanoic acid methyl ester 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:

(5R,6S)-5-(2-Benzyloxy-ethyl)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-tetrahydro-pyran-2-one (83061-04-5) → (3R,4S)-4-[(2S,3R,5S)-3-((4E,6E)-(2R,3S,8R,9R)-3,9-Dihydroxy-2,6-dimethyl-8-trityloxymethyl-undeca-4,6-dienyl)-5-methoxy-tetrahydro-furan-2-yl]-3-hydroxy-pentanoic acid methyl ester (83114-35-6)

Guidance literature:

Multi-step reaction with 12 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

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

DOI:10.1021/ja00385a038

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) → (3S,4S)-4-[(2S,3R,5S)-3-((4E,6E)-(2R,3S,8R,9R)-3,9-Dihydroxy-2,6-dimethyl-8-trityloxymethyl-undeca-4,6-dienyl)-5-methoxy-tetrahydro-furan-2-yl]-3-hydroxy-pentanoic acid methyl ester (81114-71-8,83114-35-6,83114-36-7)

Guidance literature:

Multi-step reaction with 12 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

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

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 → (3R,4S)-4-[(2S,3R,5S)-3-((4E,6E)-(2R,3S,8R,9R)-3,9-Dihydroxy-2,6-dimethyl-8-trityloxymethyl-undeca-4,6-dienyl)-5-methoxy-tetrahydro-furan-2-yl]-3-hydroxy-pentanoic acid methyl ester (83114-35-6)

Guidance literature:

Multi-step reaction with 11 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

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

DOI:10.1021/ja00385a038

upstream raw materials:

diazomethane

(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

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

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

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

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