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

Base Information

• Chemical Name: (2R,3S,4R,5S)-1-(tert-Butyl-diphenyl-silanyloxy)-5-[1,3]dithian-2-yl-3-methyl-hexane-2,4-diol
• CAS No.: 381247-11-6
• Molecular Formula: C₂₇H₄₀O₃S₂Si
• Molecular Weight: 504.83
• Mol file: 381247-11-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about (2R,3S,4R,5S)-1-(tert-Butyl-diphenyl-silanyloxy)-5-[1,3]dithian-2-yl-3-methyl-hexane-2,4-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: 88.0%

tert-butylchlorodiphenylsilane (58479-61-1) + (2R,3S,4R,5S)-5-[1,3]Dithian-2-yl-3-methyl-hexane-1,2,4-triol (381247-10-5) → (2R,3S,4R,5S)-1-(tert-Butyl-diphenyl-silanyloxy)-5-[1,3]dithian-2-yl-3-methyl-hexane-2,4-diol (381247-11-6)

Guidance literature:

With 1H-imidazole; In tetrahydrofuran; for 2h;

DOI:10.1021/ja011452u

Reference yield:

(2R,3R,4R,5S,6S)-6-Benzyloxymethoxy-2,7-dihydroxy-4-methoxymethoxy-3,5-dimethyl-heptanoic acid methyl ester (235791-67-0) → (2R,3S,4R,5S)-1-(tert-Butyl-diphenyl-silanyloxy)-5-[1,3]dithian-2-yl-3-methyl-hexane-2,4-diol (381247-11-6)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂ / Pd(OH)2/C / methanol / 3 h / 20 °C / 760.05 Torr

2: NaIO₄ / methanol; H₂O / 2 h

3: 883 mg / BF₃*Et₂O / CH₂Cl₂ / 3.5 h / 0 °C

4: 95 percent / NaBH₄ / H₂O; tetrahydrofuran / 2 h

5: 88 percent / imidazole / tetrahydrofuran / 2 h

With 1H-imidazole; sodium tetrahydroborate; sodium periodate; boron trifluoride diethyl etherate; hydrogen; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1021/ja011452u

Reference yield:

(2R,3R,4R,5S,6S)-6-[(benzyloxy)methoxy]-7-(tert-butyldiphenylsilanyloxy)-2-hydroxy-4-methoxymethoxy-3,5-dimethylheptanoic acid methyl ester (195377-39-0) → (2R,3S,4R,5S)-1-(tert-Butyl-diphenyl-silanyloxy)-5-[1,3]dithian-2-yl-3-methyl-hexane-2,4-diol (381247-11-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 95 percent / TBAF; AcOH / tetrahydrofuran / 21 h / 20 °C

2: H₂ / Pd(OH)2/C / methanol / 3 h / 20 °C / 760.05 Torr

3: NaIO₄ / methanol; H₂O / 2 h

4: 883 mg / BF₃*Et₂O / CH₂Cl₂ / 3.5 h / 0 °C

5: 95 percent / NaBH₄ / H₂O; tetrahydrofuran / 2 h

6: 88 percent / imidazole / tetrahydrofuran / 2 h

With 1H-imidazole; sodium tetrahydroborate; sodium periodate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; acetic acid; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1021/ja011452u

upstream raw materials:

tert-butylchlorodiphenylsilane

(2R,3S,4R,5S)-5-[1,3]Dithian-2-yl-3-methyl-hexane-1,2,4-triol

(2R,3R,4R,5S,6S)-6-[(benzyloxy)methoxy]-7-(tert-butyldiphenylsilanyloxy)-2-hydroxy-4-methoxymethoxy-3,5-dimethylheptanoic acid methyl ester

(2R,3R,4R,5S,6S)-6-Benzyloxymethoxy-2,7-dihydroxy-4-methoxymethoxy-3,5-dimethyl-heptanoic acid methyl ester

Downstream raw materials:

(4R,5S,6R)-4-((S)-1-{2-[(2R,3S,4R)-2,4-bis(tert-butyldimethylsilanyloxy)-3,5-dimethylhexyl]-[1,3]dithian-2-yl}-ethyl)-6-(tert-butyldiphenylsilanyloxymethyl)-2,2,5-trimethyl-[1,3]dioxane

tert-butyl-[(4R,5S,6R)-6-((S)-1-[1,3]dithian-2-yl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl-methoxy]-diphenylsilane