(3R,4R,5S,6S)-3-Acetoxy-4-benzyloxy-6-hydroxy-3,5-dimethyl-non-8-enoic acid benzyl ester

Base Information

Chemical Name:(3R,4R,5S,6S)-3-Acetoxy-4-benzyloxy-6-hydroxy-3,5-dimethyl-non-8-enoic acid benzyl ester
CAS No.:161926-46-1
Molecular Formula:C₂₇H₃₄O₆
Molecular Weight:454.563
Hs Code.:

Synonyms:(3R,4R,5S,6S)-3-Acetoxy-4-benzyloxy-6-hydroxy-3,5-dimethyl-non-8-enoic acid benzyl ester

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Chemical Property of (3R,4R,5S,6S)-3-Acetoxy-4-benzyloxy-6-hydroxy-3,5-dimethyl-non-8-enoic acid benzyl ester

Chemical Property:

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Technology Process of (3R,4R,5S,6S)-3-Acetoxy-4-benzyloxy-6-hydroxy-3,5-dimethyl-non-8-enoic acid benzyl ester

There total 8 articles about (3R,4R,5S,6S)-3-Acetoxy-4-benzyloxy-6-hydroxy-3,5-dimethyl-non-8-enoic 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:

: (E)-(5S,6R,7R)-6-Benzyloxy-7-hydroxy-5,7-dimethyl-non-3-enedioic acid 9-benzyl ester 1-methyl ester

: 161926-46-1
(3R,4R,5S,6S)-3-Acetoxy-4-benzyloxy-6-hydroxy-3,5-dimethyl-non-8-enoic acid benzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: Et₃N; DMAP / 0 °C

2: 88 percent / O₃; Me₂S / -78 °C

3: TiCl₄

With dmap; dimethylsulfide; titanium tetrachloride; ozone; triethylamine; 1: Acetylation / 2: ozonolysis / 3: Addition;
DOI:10.1021/jo971793j

Reference yield:

: 140-11-4
Benzyl acetate

: 161926-46-1
(3R,4R,5S,6S)-3-Acetoxy-4-benzyloxy-6-hydroxy-3,5-dimethyl-non-8-enoic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) LiN(TMS)2 / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -78 deg C, 1 h

2: DMAP, Et₃N / CH₂Cl₂ / 48 h / 0 °C

3: 1.) O₃, pyridine, 2.) Me₂S / 1.) MeOH, CH₂Cl₂, -78 deg C, 2.) MeOH, CH₂Cl₂, RT, 12 h

4: 1.) TiCl₄ / 1.) CH₂Cl₂, -78 deg C, 5 min, 2.) CH₂Cl₂, -78 deg C, 16 h

With pyridine; dmap; dimethylsulfide; titanium tetrachloride; ozone; triethylamine; lithium hexamethyldisilazane; In dichloromethane;
DOI:10.1021/ja9743194

Reference yield:

: (E)-(S)-6-Benzyloxy-5-methyl-7-oxo-oct-3-enoic acid methyl ester

: 161926-46-1
(3R,4R,5S,6S)-3-Acetoxy-4-benzyloxy-6-hydroxy-3,5-dimethyl-non-8-enoic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) LiN(TMS)2 / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -78 deg C, 1 h

2: DMAP, Et₃N / CH₂Cl₂ / 48 h / 0 °C

3: 1.) O₃, pyridine, 2.) Me₂S / 1.) MeOH, CH₂Cl₂, -78 deg C, 2.) MeOH, CH₂Cl₂, RT, 12 h

4: 1.) TiCl₄ / 1.) CH₂Cl₂, -78 deg C, 5 min, 2.) CH₂Cl₂, -78 deg C, 16 h

With pyridine; dmap; dimethylsulfide; titanium tetrachloride; ozone; triethylamine; lithium hexamethyldisilazane; In dichloromethane;
DOI:10.1021/ja9743194