(1S,4S,5R)-10-Benzyloxy-1-{(2R,3R,5S)-3-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-tetrahydro-furan-2-yl}-decane-1,4,5-triol

Base Information

• Chemical Name: (1S,4S,5R)-10-Benzyloxy-1-{(2R,3R,5S)-3-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-tetrahydro-furan-2-yl}-decane-1,4,5-triol
• CAS No.: 879290-57-0
• Molecular Formula: C₅₁H₉₈O₇Si₂
• Molecular Weight: 879.506
• Mol file: 879290-57-0.mol

Synonyms:(1S,4S,5R)-10-Benzyloxy-1-{(2R,3R,5S)-3-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-tetrahydro-furan-2-yl}-decane-1,4,5-triol

Chemical Property of (1S,4S,5R)-10-Benzyloxy-1-{(2R,3R,5S)-3-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-tetrahydro-furan-2-yl}-decane-1,4,5-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4S,5R)-10-Benzyloxy-1-{(2R,3R,5S)-3-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-tetrahydro-furan-2-yl}-decane-1,4,5-triol

There total 29 articles about (1S,4S,5R)-10-Benzyloxy-1-{(2R,3R,5S)-3-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-tetrahydro-furan-2-yl}-decane-1,4,5-triol 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: 73.0%

(Z)-(S)-10-Benzyloxy-1-{(2R,3R,5S)-3-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-tetrahydro-furan-2-yl}-dec-4-en-1-ol (879290-47-8) → (1S,4S,5R)-10-Benzyloxy-1-{(2R,3R,5S)-3-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-tetrahydro-furan-2-yl}-decane-1,4,5-triol (879290-57-0) + (1S,4R,5S)-10-Benzyloxy-1-{(2R,3R,5S)-3-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-tetrahydro-furan-2-yl}-decane-1,4,5-triol (879290-49-0)

Guidance literature:

With AD-mix-α; methanesulfonamide; water; potassium osmate(VI); In tert-butyl alcohol; at 0 ℃; for 16h;

DOI:10.1021/jo052073c

Reference yield:

(Z)-(S)-10-Benzyloxy-1-{(2R,3R,5S)-3-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-tetrahydro-furan-2-yl}-dec-4-en-1-ol (879290-47-8) → (1S,4S,5R)-10-Benzyloxy-1-{(2R,3R,5S)-3-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-tetrahydro-furan-2-yl}-decane-1,4,5-triol (879290-57-0)

Guidance literature:

With methanesulfonamide; AD-mix-β; water; potassium osmate(VI); In tert-butyl alcohol; at 0 ℃; for 16h;

DOI:10.1021/jo052073c

Reference yield:

((Z)-9-Benzyloxy-non-3-enyloxy)-trimethyl-silane → (1S,4S,5R)-10-Benzyloxy-1-{(2R,3R,5S)-3-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-tetrahydro-furan-2-yl}-decane-1,4,5-triol (879290-57-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 9 g / acetic acid; H₂O / tetrahydrofuran; toluene / 15 h / 20 °C

2.1: triethylamine / CH₂Cl₂ / 0.5 h / 0 °C

3.1: 10.1 g / sodium iodide / acetone / 2 h / Heating

4.1: t-BuLi / diethyl ether; pentane / 0.25 h / -100 - -90 °C

4.2: MgBr₂*OEt₂ / diethyl ether; pentane / 1 h / -90 - 0 °C

4.3: 85 percent / MgBr₂*OEt₂ / diethyl ether; pentane / -40 °C

5.1: AD-mix-β; methanesulfonamide; water / K2OsO4*2H2O / 2-methyl-propan-2-ol / 16 h / 0 °C

With methanesulfonamide; AD-mix-β; water; tert.-butyl lithium; acetic acid; triethylamine; sodium iodide; potassium osmate(VI); In tetrahydrofuran; diethyl ether; dichloromethane; acetone; toluene; tert-butyl alcohol; pentane; 5.1: Sharpless asymmetric dihydroxylation;

DOI:10.1021/jo052073c

upstream raw materials:

(Z)-(S)-10-Benzyloxy-1-{(2R,3R,5S)-3-(tert-butyl-dimethyl-silanyloxy)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-tetrahydro-furan-2-yl}-dec-4-en-1-ol

(Z)-9-Benzyloxy-non-3-en-1-ol

((Z)-9-Iodo-non-6-enyloxymethyl)-benzene

(E)-Henicos-3-en-1-ol

Downstream raw materials:

(R)-6-Benzyloxy-1-{(2S,5R,2'R,3'R,5'S)-3'-(tert-butyl-dimethyl-silanyloxy)-5'-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-octadecyl]-octahydro-[2,2']bifuranyl-5-yl}-hexan-1-ol