(2R,3S,4S,5R)-1,6-bis(benzyloxy)-5-(tert-butyldiphenylsilyloxy)-3,4-dihydroxyhexan-2-yl methanesulfonate

Base Information

• Chemical Name: (2R,3S,4S,5R)-1,6-bis(benzyloxy)-5-(tert-butyldiphenylsilyloxy)-3,4-dihydroxyhexan-2-yl methanesulfonate
• CAS No.: 847659-90-9
• Molecular Formula: C₃₇H₄₆O₈SSi
• Molecular Weight: 678.919

Synonyms:(2R,3S,4S,5R)-1,6-bis(benzyloxy)-5-(tert-butyldiphenylsilyloxy)-3,4-dihydroxyhexan-2-yl methanesulfonate

Chemical Property of (2R,3S,4S,5R)-1,6-bis(benzyloxy)-5-(tert-butyldiphenylsilyloxy)-3,4-dihydroxyhexan-2-yl methanesulfonate

Chemical Property:

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Technology Process of (2R,3S,4S,5R)-1,6-bis(benzyloxy)-5-(tert-butyldiphenylsilyloxy)-3,4-dihydroxyhexan-2-yl methanesulfonate

There total 1 articles about (2R,3S,4S,5R)-1,6-bis(benzyloxy)-5-(tert-butyldiphenylsilyloxy)-3,4-dihydroxyhexan-2-yl methanesulfonate 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: 85.0%

(4S,4'S,5R,5'R)-5'-(tert-butyldiphenylsilyloxy)-2,2'-diphenyl-4,4'-bi(1,3-dioxan)-5-yl methanesulfonate (847659-89-6) → (2R,3S,4S,5R)-1,6-bis(benzyloxy)-5-(tert-butyldiphenylsilyloxy)-3,4-dihydroxyhexan-2-yl methanesulfonate (847659-90-9)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 0.5h; regioselective reaction;

DOI:10.1021/jo900030p

Reference yield: 86.0%

methyl iodide (74-88-4) + (2R,3S,4S,5R)-1,6-bis(benzyloxy)-5-(tert-butyldiphenylsilyloxy)-3,4-dihydroxyhexan-2-yl methanesulfonate (847659-90-9) → {(1S,2R)-3-benzyloxy-1-[(2R,3S)-3-(benzyloxymethyl)oxiran-2-yl]-1-methoxypropan-2-yloxy}(tert-butyl)diphenylsilane (1360594-40-6)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 0 ℃; for 6h; Inert atmosphere;

DOI:10.1002/ejoc.201100968

Reference yield: 80.0%

2,2-dimethoxy-propane (77-76-9) + (2R,3S,4S,5R)-1,6-bis(benzyloxy)-5-(tert-butyldiphenylsilyloxy)-3,4-dihydroxyhexan-2-yl methanesulfonate (847659-90-9) → (R)-2-(benzyloxy)-1-((4S,5S)-5-((R)-2-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)ethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl methanesulfonate (1138325-27-5)

Guidance literature:

With camphor-10-sulfonic acid; In acetone; at 20 ℃; for 4h;

DOI:10.1021/jo900030p

upstream raw materials:

(4S,4'S,5R,5'R)-5'-(tert-butyldiphenylsilyloxy)-2,2'-diphenyl-4,4'-bi(1,3-dioxan)-5-yl methanesulfonate

Downstream raw materials:

(R)-2-(benzyloxy)-1-((4S,5S)-5-((R)-2-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)ethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl methanesulfonate

{(1S,2R)-3-benzyloxy-1-[(2R,3S)-3-(benzyloxymethyl)oxiran-2-yl]-1-methoxypropan-2-yloxy}(tert-butyl)diphenylsilane

(R)-1-((4S,5S)-5-((R)-1-(tert-butyldiphenylsilyloxy)-2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl methanesulfonate

(R)-2-(tert-butyldiphenylsilyloxy)-1-((4R,5R)-2,2-dimethyl-5-((S)-oxiran-2-yl)-1,3-dioxolan-4-yl)ethanol

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