(2S,5S,7S)-1-benzyloxy-7-(tert-butyldimethylsilanyloxy)-8-{(2R,6S)-6-[2-(tert-butyldimethylsilanyloxy)ethyl]tetrahydropyran-2-yl}-5-hydroxy-2-methyloctan-3-one

Base Information

• Chemical Name: (2S,5S,7S)-1-benzyloxy-7-(tert-butyldimethylsilanyloxy)-8-{(2R,6S)-6-[2-(tert-butyldimethylsilanyloxy)ethyl]tetrahydropyran-2-yl}-5-hydroxy-2-methyloctan-3-one
• CAS No.: 866021-68-3
• Molecular Formula: C₃₅H₆₄O₆Si₂
• Molecular Weight: 637.061

Synonyms:(2S,5S,7S)-1-benzyloxy-7-(tert-butyldimethylsilanyloxy)-8-{(2R,6S)-6-[2-(tert-butyldimethylsilanyloxy)ethyl]tetrahydropyran-2-yl}-5-hydroxy-2-methyloctan-3-one

Chemical Property of (2S,5S,7S)-1-benzyloxy-7-(tert-butyldimethylsilanyloxy)-8-{(2R,6S)-6-[2-(tert-butyldimethylsilanyloxy)ethyl]tetrahydropyran-2-yl}-5-hydroxy-2-methyloctan-3-one

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5S,7S)-1-benzyloxy-7-(tert-butyldimethylsilanyloxy)-8-{(2R,6S)-6-[2-(tert-butyldimethylsilanyloxy)ethyl]tetrahydropyran-2-yl}-5-hydroxy-2-methyloctan-3-one

There total 8 articles about (2S,5S,7S)-1-benzyloxy-7-(tert-butyldimethylsilanyloxy)-8-{(2R,6S)-6-[2-(tert-butyldimethylsilanyloxy)ethyl]tetrahydropyran-2-yl}-5-hydroxy-2-methyloctan-3-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:

((2R,6S)-6-allyltetrahydropyran-2-yl)acetic acid ethyl ester (866021-62-7) → (2S,5S,7S)-1-benzyloxy-7-(tert-butyldimethylsilanyloxy)-8-{(2R,6S)-6-[2-(tert-butyldimethylsilanyloxy)ethyl]tetrahydropyran-2-yl}-5-hydroxy-2-methyloctan-3-one (866021-68-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: O₃ / CH₂Cl₂ / -78 °C

1.2: NaBH₄

2.1: imidazole; DMAP / dimethylformamide

3.1: LiAlH₄ / diethyl ether / -78 °C

4.1: (COCl)2; DMSO; Et₃N

5.1: diethyl ether / -78 °C

6.1: imidazole; DMAP / dimethylformamide

7.1: O₃ / CH₂Cl₂ / -78 °C

7.2: PPh₃ / CH₂Cl₂

8.1: (-)-Ipc₂BCl; Et₃N / diethyl ether / -78 °C

8.3: 68 percent / aq. H₂O₂; pH 7 buffer / methanol / pH 7

With 1H-imidazole; dmap; lithium aluminium tetrahydride; oxalyl dichloride; ozone; dimethyl sulfoxide; triethylamine; (-)-diisopinocamphenylborane chloride; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; 4.1: Swern oxidation;

DOI:10.1021/ol051405x

Reference yield:

[(2R,6S)-6-(2-hydroxyethyl)tetrahydropyran-2-yl]acetic acid ethyl ester (866021-89-8) → (2S,5S,7S)-1-benzyloxy-7-(tert-butyldimethylsilanyloxy)-8-{(2R,6S)-6-[2-(tert-butyldimethylsilanyloxy)ethyl]tetrahydropyran-2-yl}-5-hydroxy-2-methyloctan-3-one (866021-68-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: imidazole; DMAP / dimethylformamide

2.1: LiAlH₄ / diethyl ether / -78 °C

3.1: (COCl)2; DMSO; Et₃N

4.1: diethyl ether / -78 °C

5.1: imidazole; DMAP / dimethylformamide

6.1: O₃ / CH₂Cl₂ / -78 °C

6.2: PPh₃ / CH₂Cl₂

7.1: (-)-Ipc₂BCl; Et₃N / diethyl ether / -78 °C

7.3: 68 percent / aq. H₂O₂; pH 7 buffer / methanol / pH 7

With 1H-imidazole; dmap; lithium aluminium tetrahydride; oxalyl dichloride; ozone; dimethyl sulfoxide; triethylamine; (-)-diisopinocamphenylborane chloride; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; 3.1: Swern oxidation;

DOI:10.1021/ol051405x

Reference yield:

2-{(2R,6S)-6-[2-(tert-butyldimethylsilanyloxy)ethyl]tetrahydropyran-2-yl}ethanal (866021-65-0) → (2S,5S,7S)-1-benzyloxy-7-(tert-butyldimethylsilanyloxy)-8-{(2R,6S)-6-[2-(tert-butyldimethylsilanyloxy)ethyl]tetrahydropyran-2-yl}-5-hydroxy-2-methyloctan-3-one (866021-68-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: diethyl ether / -78 °C

2.1: imidazole; DMAP / dimethylformamide

3.1: O₃ / CH₂Cl₂ / -78 °C

3.2: PPh₃ / CH₂Cl₂

4.1: (-)-Ipc₂BCl; Et₃N / diethyl ether / -78 °C

4.3: 68 percent / aq. H₂O₂; pH 7 buffer / methanol / pH 7

With 1H-imidazole; dmap; ozone; triethylamine; (-)-diisopinocamphenylborane chloride; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol051405x

upstream raw materials:

((2R,6S)-6-allyltetrahydropyran-2-yl)acetic acid ethyl ester

[(2R,6S)-6-(2-hydroxyethyl)tetrahydropyran-2-yl]acetic acid ethyl ester

2-{(2R,6S)-6-[2-(tert-butyldimethylsilanyloxy)ethyl]tetrahydropyran-2-yl}ethanal

2-{(2R,6S)-6-[2-(tert-butyldimethylsilanyloxy)ethyl]tetrahydropyran-2-yl}ethanol

Downstream raw materials:

C₆₀H₁₀₈O₁₂Si₃

C₆₀H₁₁₀O₁₂Si₃

C₆₀H₁₁₀O₁₂Si₃

(4R,6R)-4-((S)-2-benzyloxy-1-methylethyl)-6-((R)-2-(tert-butyldimethylsilanyloxy)-3-{(2R,6S)-6-[2-(tert-butyldimethylsilanyloxy)ethyl]tetrahydropyran-2-yl}propyl)-2,2-dimethyl-[1,3]dioxane

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