(1S,2S,3R)-1-[4-(tert-Butyl-diphenyl-silanyloxymethyl)-phenyl]-2-hydroxymethyl-butane-1,3-diol

Base Information

• Chemical Name: (1S,2S,3R)-1-[4-(tert-Butyl-diphenyl-silanyloxymethyl)-phenyl]-2-hydroxymethyl-butane-1,3-diol
• CAS No.: 196880-50-9
• Molecular Formula: C₂₈H₃₆O₄Si
• Molecular Weight: 464.677

Synonyms:(1S,2S,3R)-1-[4-(tert-Butyl-diphenyl-silanyloxymethyl)-phenyl]-2-hydroxymethyl-butane-1,3-diol

Chemical Property of (1S,2S,3R)-1-[4-(tert-Butyl-diphenyl-silanyloxymethyl)-phenyl]-2-hydroxymethyl-butane-1,3-diol

Chemical Property:

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Technology Process of (1S,2S,3R)-1-[4-(tert-Butyl-diphenyl-silanyloxymethyl)-phenyl]-2-hydroxymethyl-butane-1,3-diol

There total 4 articles about (1S,2S,3R)-1-[4-(tert-Butyl-diphenyl-silanyloxymethyl)-phenyl]-2-hydroxymethyl-butane-1,3-diol 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: 92.0%

(2R,5R,6R)-2-tert-Butyl-5-{(S)-[4-(tert-butyl-diphenyl-silanyloxymethyl)-phenyl]-hydroxy-methyl}-6-methyl-[1,3]dioxan-4-one (196880-48-5) → (1S,2S,3R)-1-[4-(tert-Butyl-diphenyl-silanyloxymethyl)-phenyl]-2-hydroxymethyl-butane-1,3-diol (196880-50-9)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; methanol; for 18h; Ambient temperature;

DOI:10.1002/hlca.19970800522

Reference yield:

4-({[tert-butyl(diphenyl)silyl]oxy}methyl)benzaldehyde (196880-47-4) → (1S,2S,3R)-1-[4-(tert-Butyl-diphenyl-silanyloxymethyl)-phenyl]-2-hydroxymethyl-butane-1,3-diol (196880-50-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) (i-Pr)2NH, BuLi / 1.) THF, 0 deg C, 15 min; 2.) THF, -78 deg C, 45 min; 3.) THF, -78 deg C, 3 h

2: 92 percent / NaBH₄ / tetrahydrofuran; methanol / 18 h / Ambient temperature

With sodium tetrahydroborate; n-butyllithium; diisopropylamine; In tetrahydrofuran; methanol;

DOI:10.1002/hlca.19970800522

Reference yield:

[4-({[tert-butyl(diphenyl)silyl]oxy}methyl)phenyl]methanol (146952-73-0) → (1S,2S,3R)-1-[4-(tert-Butyl-diphenyl-silanyloxymethyl)-phenyl]-2-hydroxymethyl-butane-1,3-diol (196880-50-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / PDC / CH₂Cl₂ / 3 h / Ambient temperature

2: 1.) (i-Pr)2NH, BuLi / 1.) THF, 0 deg C, 15 min; 2.) THF, -78 deg C, 45 min; 3.) THF, -78 deg C, 3 h

3: 92 percent / NaBH₄ / tetrahydrofuran; methanol / 18 h / Ambient temperature

With sodium tetrahydroborate; dipyridinium dichromate; n-butyllithium; diisopropylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1002/hlca.19970800522

upstream raw materials:

(2R,6R)-2-tert-butyl-6-methyl-1,3-dioxan-4-one

4-({[tert-butyl(diphenyl)silyl]oxy}methyl)benzaldehyde

(2R,5R,6R)-2-tert-Butyl-5-{(S)-[4-(tert-butyl-diphenyl-silanyloxymethyl)-phenyl]-hydroxy-methyl}-6-methyl-[1,3]dioxan-4-one

[4-({[tert-butyl(diphenyl)silyl]oxy}methyl)phenyl]methanol

Downstream raw materials:

tert-Butyl-[4-((1S,2S,3R)-1,3-dimethoxy-2-methoxymethyl-butyl)-benzyloxy]-diphenyl-silane

C₅₇H₈₃BrO₁₂

(4-{(1S,2S,3R)-1,3-Bis-[4-((1R,2S,3R)-1,3-dimethoxy-2-methoxymethyl-butyl)-benzyloxy]-2-[4-((1R,2S,3R)-1,3-dimethoxy-2-methoxymethyl-butyl)-benzyloxymethyl]-butyl}-phenyl)-methanol

(4-{(1S,2S,3R)-1,3-Bis-[4-((1S,2S,3R)-1,3-dimethoxy-2-methoxymethyl-butyl)-benzyloxy]-2-[4-((1S,2S,3R)-1,3-dimethoxy-2-methoxymethyl-butyl)-benzyloxymethyl]-butyl}-phenyl)-methanol

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