(3S,5S)-6-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)-3,5-dihydroxyhexane

Base Information

• Chemical Name: (3S,5S)-6-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)-3,5-dihydroxyhexane
• CAS No.: 153025-58-2
• Molecular Formula: C₂₉H₃₈O₄Si
• Molecular Weight: 478.704
• Mol file: 153025-58-2.mol

Synonyms:(3S,5S)-6-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)-3,5-dihydroxyhexane

Chemical Property of (3S,5S)-6-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)-3,5-dihydroxyhexane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,5S)-6-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)-3,5-dihydroxyhexane

There total 2 articles about (3S,5S)-6-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)-3,5-dihydroxyhexane 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: 95.0%

2,4-dideoxy-6-O-(phenylmethyl)-D-erythro-hexitol (81120-67-4) + tert-butylchlorodiphenylsilane (58479-61-1) → (3S,5S)-6-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)-3,5-dihydroxyhexane (153025-58-2)

Guidance literature:

With 1H-imidazole;

DOI:10.1016/S0040-4039(00)92381-5

Reference yield:

(3S,4S,5R)-tert-butyl <6-(benzyloxy)-4,5-epoxy-3-hydroxy>hexanoate (138747-45-2) → (3S,5S)-6-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)-3,5-dihydroxyhexane (153025-58-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / RedAl / tetrahydrofuran / 4 h

2: 95 percent / imidazole / dimethylformamide / 12 h

With 1H-imidazole; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)82375-9

Reference yield: 100.0%

(3S,5S)-6-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)-3,5-dihydroxyhexane (153025-58-2) + 2,2-dimethoxy-propane (77-76-9) → (3S,5S)-6-<(benzyloxy)methyl>-4-<1-(tert-butyldiphenylsilyloxy)ethyl>-2,2-dimethyl-1,3-dioxacyclohexane (112497-22-0)

Guidance literature:

With camphor-10-sulfonic acid; for 1h;

DOI:10.1016/S0040-4020(01)82375-9

upstream raw materials:

2,4-dideoxy-6-O-(phenylmethyl)-D-erythro-hexitol

tert-butylchlorodiphenylsilane

(3S,4S,5R)-tert-butyl <6-(benzyloxy)-4,5-epoxy-3-hydroxy>hexanoate

Downstream raw materials:

(3S,5S)-6-<(benzyloxy)methyl>-4-<1-(tert-butyldiphenylsilyloxy)ethyl>-2,2-dimethyl-1,3-dioxacyclohexane

(4R,6S)-6-(benzyloxy)methyl-4-hydroxy-tetrahydro-2-pyrone

(4S,6S)-6-<(benzyloxy)methyl>-4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxacyclohexane

(3R,5S)-6-Benzyloxy-3,5-dihydroxy-hexanoic acid