(3R,4R,5S,6S,7S)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3,5,7-trimethyl-octan-2-one

Base Information

Chemical Name:(3R,4R,5S,6S,7S)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3,5,7-trimethyl-octan-2-one
CAS No.:870773-87-8
Molecular Formula:C₃₁H₅₈O₅Si₂
Molecular Weight:566.97
Hs Code.:

Synonyms:(3R,4R,5S,6S,7S)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3,5,7-trimethyl-octan-2-one

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Chemical Property of (3R,4R,5S,6S,7S)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3,5,7-trimethyl-octan-2-one

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Technology Process of (3R,4R,5S,6S,7S)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3,5,7-trimethyl-octan-2-one

There total 14 articles about (3R,4R,5S,6S,7S)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3,5,7-trimethyl-octan-2-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:

: (3S,4S,5S,6S,7S)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3,5,7-trimethyl-octan-2-ol

: 870773-87-8
(3R,4R,5S,6S,7S)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3,5,7-trimethyl-octan-2-one

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 ℃;
DOI:10.1016/j.tetlet.2006.01.105

Reference yield:

: (E)-(4S,5R,6S)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-hept-2-en-1-ol

: 870773-87-8
(3R,4R,5S,6S,7S)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3,5,7-trimethyl-octan-2-one

Guidance literature:: Multi-step reaction with 7 steps

1: m-CPBA / CH₂Cl₂ / 0 °C

2: 87 percent / tetrahydrofuran / -78 - -20 °C

3: 85 percent / PPTS / CH₂Cl₂ / 20 °C

4: DIBAL-H / CH₂Cl₂ / -78 °C

5: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

6: tetrahydrofuran / -78 °C

7: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

With oxalyl dichloride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; 5: Swern oxidation / 7: Swern oxidation;
DOI:10.1016/j.tetlet.2006.01.105

Reference yield:

: 936637-19-3
(2R,3S,4S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentanoic acid methoxy-methyl-amide

: 870773-87-8
(3R,4R,5S,6S,7S)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-3,5,7-trimethyl-octan-2-one

Guidance literature:: Multi-step reaction with 10 steps

1: DIBAL-H / tetrahydrofuran / -78 °C

2: NaH / tetrahydrofuran / -78 °C

3: DIBAL-H / CH₂Cl₂ / -78 °C

4: m-CPBA / CH₂Cl₂ / 0 °C

5: 87 percent / tetrahydrofuran / -78 - -20 °C

6: 85 percent / PPTS / CH₂Cl₂ / 20 °C

7: DIBAL-H / CH₂Cl₂ / -78 °C

8: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

9: tetrahydrofuran / -78 °C

10: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

With oxalyl dichloride; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; 2: Horner-Waddsworth-Emmons homologation / 8: Swern oxidation / 10: Swern oxidation;
DOI:10.1016/j.tetlet.2006.01.105