(2R,5S,6S,7S)-1-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-8,8-dimethoxy-5,7-dimethyl-octan-4-one

Base Information

• Chemical Name: (2R,5S,6S,7S)-1-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-8,8-dimethoxy-5,7-dimethyl-octan-4-one
• CAS No.: 172269-44-2
• Molecular Formula: C₂₅H₄₄O₆Si
• Molecular Weight: 468.706

Synonyms:(2R,5S,6S,7S)-1-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-8,8-dimethoxy-5,7-dimethyl-octan-4-one

Chemical Property of (2R,5S,6S,7S)-1-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-8,8-dimethoxy-5,7-dimethyl-octan-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,5S,6S,7S)-1-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-8,8-dimethoxy-5,7-dimethyl-octan-4-one

There total 10 articles about (2R,5S,6S,7S)-1-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-8,8-dimethoxy-5,7-dimethyl-octan-4-one 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: 80.0%

(R)-1-Benzyloxy-3-{2-[(1S,2S,3S)-2-(tert-butyl-dimethyl-silanyloxy)-4,4-dimethoxy-1,3-dimethyl-butyl]-[1,3]dithian-2-yl}-propan-2-ol (172269-24-8) → (2R,5S,6S,7S)-1-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-8,8-dimethoxy-5,7-dimethyl-octan-4-one (172269-44-2)

Guidance literature:

With bis-[(trifluoroacetoxy)iodo]benzene; In methanol; water;

DOI:10.1021/ja00153a030

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (2R,5S,6S,7S)-1-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-8,8-dimethoxy-5,7-dimethyl-octan-4-one (172269-44-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 100 percent / 2,6-lutidine / CH₂Cl₂

2: 92 percent / H₂ / Pd(OH)2/C / ethanol

3: 98 percent / SO₃*pyridine, Et₃N / dimethylsulfoxide

4: 79 percent / ZnCl₂ / diethyl ether

5: 91 percent / DIBAL / tetrahydrofuran

6: 99 percent / TsOH*H₂O / methanol

7: 1.) t-BuLi, HMPA / 1.) THF, 2.) THF

8: 80 percent / PhI(CF₃CO₃)2 / methanol; H₂O

With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; pyridine-SO₃ complex; hydrogen; tert.-butyl lithium; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; bis-[(trifluoroacetoxy)iodo]benzene; zinc(II) chloride; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; dimethyl sulfoxide;

DOI:10.1021/ja00153a030

Reference yield:

(2S,3R,4R)-3-Hydroxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-pentanoic acid methoxy-methyl-amide (172269-19-1) → (2R,5S,6S,7S)-1-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-8,8-dimethoxy-5,7-dimethyl-octan-4-one (172269-44-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 100 percent / 2,6-lutidine / CH₂Cl₂

2: 92 percent / H₂ / Pd(OH)2/C / ethanol

3: 98 percent / SO₃*pyridine, Et₃N / dimethylsulfoxide

4: 79 percent / ZnCl₂ / diethyl ether

5: 91 percent / DIBAL / tetrahydrofuran

6: 99 percent / TsOH*H₂O / methanol

7: 1.) t-BuLi, HMPA / 1.) THF, 2.) THF

8: 80 percent / PhI(CF₃CO₃)2 / methanol; H₂O

With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; pyridine-SO₃ complex; hydrogen; tert.-butyl lithium; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; bis-[(trifluoroacetoxy)iodo]benzene; zinc(II) chloride; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; dimethyl sulfoxide;

DOI:10.1021/ja00153a030

upstream raw materials:

(R)-1-Benzyloxy-3-{2-[(1S,2S,3S)-2-(tert-butyl-dimethyl-silanyloxy)-4,4-dimethoxy-1,3-dimethyl-butyl]-[1,3]dithian-2-yl}-propan-2-ol

t-butyldimethylsiyl triflate

tert-Butyl-[(1S,2S)-1-((S)-1-[1,3]dithian-2-yl-ethyl)-3,3-dimethoxy-2-methyl-propoxy]-dimethyl-silane

(2S,3R,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-2,4-dimethyl-pentanoic acid methoxy-methyl-amide

Downstream raw materials:

C₆₃H₁₂₂O₈SSi₄

C₆₃H₁₂₀O₈SSi₄

C₆₄H₁₁₈O₈Si₄

(2R,4R,5R,6R,7S)-1-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-8,8-dimethoxy-5,7-dimethyl-octane-2,4-diol

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