(1R,2S,3R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-1-[1,3]dithian-2-yl-2,4-dimethyl-pentane-1,3-diol

Base Information

• Chemical Name: (1R,2S,3R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-1-[1,3]dithian-2-yl-2,4-dimethyl-pentane-1,3-diol
• CAS No.: 114811-24-4
• Molecular Formula: C₂₇H₄₀O₃S₂Si
• Molecular Weight: 504.83
• Mol file: 114811-24-4.mol

Synonyms:(1R,2S,3R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-1-[1,3]dithian-2-yl-2,4-dimethyl-pentane-1,3-diol

Chemical Property of (1R,2S,3R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-1-[1,3]dithian-2-yl-2,4-dimethyl-pentane-1,3-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,3R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-1-[1,3]dithian-2-yl-2,4-dimethyl-pentane-1,3-diol

There total 9 articles about (1R,2S,3R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-1-[1,3]dithian-2-yl-2,4-dimethyl-pentane-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: 93.0%

(2R,3S,4R,5S)-3,5-dimethyl-2,4,6-trihydroxyhexanal trimethylene dithioacetal (78785-41-8) + tert-butylchlorodiphenylsilane (58479-61-1) → (1R,2S,3R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-1-[1,3]dithian-2-yl-2,4-dimethyl-pentane-1,3-diol (114811-24-4)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1016/S0040-4039(00)96566-3

Reference yield: 93.0%

(2S,3R,4S)-1-[1,3]Dithian-2-yl-2,4-dimethyl-pentane-1,3,5-triol (78785-41-8,124895-73-4) + tert-butylchlorodiphenylsilane (58479-61-1) → (2RS,3S,4S,5R)-6-tert-butyldiphenylsilyloxy-2,4-dihydroxy-3,5-dimethylhexanal trimethylene dithioacetal (114811-24-4,124871-57-4)

Guidance literature:

With 1H-imidazole; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1248/cpb.37.1167

Reference yield:

Benzoic acid (2R,3R,4S)-3,5-dihydroxy-2,4-dimethyl-pentyl ester → (1R,2S,3R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-1-[1,3]dithian-2-yl-2,4-dimethyl-pentane-1,3-diol (114811-24-4)

Guidance literature:

Multi-step reaction with 6 steps

1: CSA / CH₂Cl₂ / Ambient temperature

2: 96 percent / H₂ / Pd-C / ethanol

3: 82 percent / PCC / CH₂Cl₂ / Ambient temperature; molecular sieves

4: 86 percent / n-BuLi / tetrahydrofuran / -75 - -70 °C

5: 92 percent / TsOH*H₂O / methanol / Ambient temperature

6: 93 percent / imidazole / dimethylformamide / Ambient temperature

With 1H-imidazole; n-butyllithium; camphor-10-sulfonic acid; hydrogen; toluene-4-sulfonic acid; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)96566-3

upstream raw materials:

(2R,3S,4R,5S)-3,5-dimethyl-2,4,6-trihydroxyhexanal trimethylene dithioacetal

tert-butylchlorodiphenylsilane

(2R,3S,4R)-3,5-(Isopropylidenedioxy)-2,4-dimethylpentanal

(2R,3S,4S,5S)-3,5-dimethyl-2-hydroxy-4,6-isopropylidenedioxyhexanal trimethylene dithioacetal

Downstream raw materials:

(2R,3S,4S,5R)-1-tert-butyldiphenylsilyloxy-2,4-dimethyl-3,5-isopropylidenedioxyheptan-6-one

(2S,4R)-2-{(4R,5S,6R)-6-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-4-{(4S,5S,6R)-6-[(1R,2R)-2-(4-methoxy-benzyloxy)-1-methoxymethoxy-1-methyl-butyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-pentan-2-ol

(2R,3S,4S,5R)-1-tert-butyldiphenylsilyloxy-2,4-dimethyl-6-hydroxy-3,5-isopropylidenedioxyheptane

(2R,3S,4S,5R,6RS,7R,9S,10S,11R,12R,13R)-3,5:9,11-bis(isopropylidenedioxy)-1-tert-butyldiphenylsilyloxy-13-(4-methoxybenzyloxy)-12-methoxymethoxy-2,4,8,10,12-pentamethyl-7-phenylsulfinylpentadecan-6-ol