(3S,6R,7S)-10-Benzyloxy-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6-trimethyl-5-oxo-decanoic acid tert-butyl ester

Base Information

Chemical Name:(3S,6R,7S)-10-Benzyloxy-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6-trimethyl-5-oxo-decanoic acid tert-butyl ester
CAS No.:192370-83-5
Molecular Formula:C₃₆H₆₆O₆Si₂
Molecular Weight:651.087
Hs Code.:

Synonyms:(3S,6R,7S)-10-Benzyloxy-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6-trimethyl-5-oxo-decanoic acid tert-butyl ester

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Chemical Property of (3S,6R,7S)-10-Benzyloxy-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6-trimethyl-5-oxo-decanoic acid tert-butyl ester

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Technology Process of (3S,6R,7S)-10-Benzyloxy-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6-trimethyl-5-oxo-decanoic acid tert-butyl ester

There total 8 articles about (3S,6R,7S)-10-Benzyloxy-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6-trimethyl-5-oxo-decanoic acid tert-butyl ester 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: 90.0%

: 192370-75-5
(3S,5S,6S,7S)-10-Benzyloxy-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-4,4,6-trimethyl-decanoic acid tert-butyl ester

: 192370-83-5
(3S,6R,7S)-10-Benzyloxy-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6-trimethyl-5-oxo-decanoic acid tert-butyl ester

Guidance literature:: With Dess-Martin periodane;
DOI:10.1016/S0040-4039(97)00931-3

Reference yield:

: 5470-84-8
4-benzyloxybutanal

: 192370-83-5
(3S,6R,7S)-10-Benzyloxy-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6-trimethyl-5-oxo-decanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 2.) aq. NaOH, H₂O₂ / 1.) Et₂O, -78 deg C

2: 2,6-lutidine / CH₂Cl₂

3: 82 percent / O₃; DMS / CH₂Cl₂; methanol / -78 °C

4: NaH, BuLi / 0 °C

5: Me₄NBH(OAc)3 / -10 °C

6: 88 percent / 2,6-lutidine / -40 °C

7: 90 percent / Dess-Martin periodinane

With 2,6-dimethylpyridine; sodium hydroxide; n-butyllithium; 2,3-dimercapto-succinic acid; dihydrogen peroxide; sodium hydride; Dess-Martin periodane; ozone; tetramethylammonium triacetoxyborohydride; In methanol; dichloromethane;
DOI:10.1016/S0040-4039(97)00931-3

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 192370-83-5
(3S,6R,7S)-10-Benzyloxy-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-4,4,6-trimethyl-5-oxo-decanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 2,6-lutidine / CH₂Cl₂

2: 82 percent / O₃; DMS / CH₂Cl₂; methanol / -78 °C

3: NaH, BuLi / 0 °C

4: Me₄NBH(OAc)3 / -10 °C

5: 88 percent / 2,6-lutidine / -40 °C

6: 90 percent / Dess-Martin periodinane

With 2,6-dimethylpyridine; n-butyllithium; 2,3-dimercapto-succinic acid; sodium hydride; Dess-Martin periodane; ozone; tetramethylammonium triacetoxyborohydride; In methanol; dichloromethane;
DOI:10.1016/S0040-4039(97)00931-3