(3R,4R,5R,6S)-3-Acetoxy-4-benzyloxy-3,5-dimethyl-8-oxo-6-triisopropylsilanyloxy-octanoic acid benzyl ester

Base Information

Chemical Name:(3R,4R,5R,6S)-3-Acetoxy-4-benzyloxy-3,5-dimethyl-8-oxo-6-triisopropylsilanyloxy-octanoic acid benzyl ester
CAS No.:161926-48-3
Molecular Formula:C₃₅H₅₂O₇Si
Molecular Weight:612.879
Hs Code.:

Synonyms:(3R,4R,5R,6S)-3-Acetoxy-4-benzyloxy-3,5-dimethyl-8-oxo-6-triisopropylsilanyloxy-octanoic acid benzyl ester

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Chemical Property of (3R,4R,5R,6S)-3-Acetoxy-4-benzyloxy-3,5-dimethyl-8-oxo-6-triisopropylsilanyloxy-octanoic acid benzyl ester

Chemical Property:

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Technology Process of (3R,4R,5R,6S)-3-Acetoxy-4-benzyloxy-3,5-dimethyl-8-oxo-6-triisopropylsilanyloxy-octanoic acid benzyl ester

There total 10 articles about (3R,4R,5R,6S)-3-Acetoxy-4-benzyloxy-3,5-dimethyl-8-oxo-6-triisopropylsilanyloxy-octanoic acid benzyl 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%

: 161926-47-2
(3R,4R,5R,6S)-3-Acetoxy-4-benzyloxy-3,5-dimethyl-6-triisopropylsilanyloxy-non-8-enoic acid benzyl ester

: 161926-48-3
(3R,4R,5R,6S)-3-Acetoxy-4-benzyloxy-3,5-dimethyl-8-oxo-6-triisopropylsilanyloxy-octanoic acid benzyl ester

Guidance literature:: With dimethylsulfide; ozone; In methanol; for 15h; -78 degC -> r.t.;
DOI:10.1016/0040-4039(94)02427-D

Reference yield:

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 161926-48-3
(3R,4R,5R,6S)-3-Acetoxy-4-benzyloxy-3,5-dimethyl-8-oxo-6-triisopropylsilanyloxy-octanoic acid benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 100 percent

2: O₃; Me₂S / -78 °C

With dimethylsulfide; ozone; 1: silylation / 2: ozonolysis;
DOI:10.1021/jo971793j

Reference yield:

: 161926-43-8
(E)-(5S,6R)-6-Benzyloxy-5-methyl-7-oxo-oct-3-enoic acid methyl ester

: 161926-48-3
(3R,4R,5R,6S)-3-Acetoxy-4-benzyloxy-3,5-dimethyl-8-oxo-6-triisopropylsilanyloxy-octanoic acid benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: LiN(TMS)2 / -78 °C

2: Et₃N; DMAP / 0 °C

3: 88 percent / O₃; Me₂S / -78 °C

4: TiCl₄

5: 100 percent

6: O₃; Me₂S / -78 °C

With dmap; dimethylsulfide; titanium tetrachloride; ozone; triethylamine; lithium hexamethyldisilazane; 1: Addition / 2: Acetylation / 3: ozonolysis / 4: Addition / 5: silylation / 6: ozonolysis;
DOI:10.1021/jo971793j