(1R,3S,4S,5R)-3-((S)-2-Benzyloxy-1-methyl-ethyl)-1,4,8-trimethyl-2,9-dioxa-bicyclo[3.3.1]non-7-en-6-one

Base Information

• Chemical Name: (1R,3S,4S,5R)-3-((S)-2-Benzyloxy-1-methyl-ethyl)-1,4,8-trimethyl-2,9-dioxa-bicyclo[3.3.1]non-7-en-6-one
• CAS No.: 85828-15-5
• Molecular Formula: C₂₀H₂₆O₄
• Molecular Weight: 330.424
• Mol file: 85828-15-5.mol

Synonyms:(1R,3S,4S,5R)-3-((S)-2-Benzyloxy-1-methyl-ethyl)-1,4,8-trimethyl-2,9-dioxa-bicyclo[3.3.1]non-7-en-6-one

Chemical Property of (1R,3S,4S,5R)-3-((S)-2-Benzyloxy-1-methyl-ethyl)-1,4,8-trimethyl-2,9-dioxa-bicyclo[3.3.1]non-7-en-6-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3S,4S,5R)-3-((S)-2-Benzyloxy-1-methyl-ethyl)-1,4,8-trimethyl-2,9-dioxa-bicyclo[3.3.1]non-7-en-6-one

There total 15 articles about (1R,3S,4S,5R)-3-((S)-2-Benzyloxy-1-methyl-ethyl)-1,4,8-trimethyl-2,9-dioxa-bicyclo[3.3.1]non-7-en-6-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: 70.0%

(S)-2-[(1S,2R,3R)-4-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1,3-dimethyl-butyl]-6-hydroxy-5,6-dimethyl-6H-pyran-3-one → (1R,3S,4S,5R)-3-((S)-2-Benzyloxy-1-methyl-ethyl)-1,4,8-trimethyl-2,9-dioxa-bicyclo[3.3.1]non-7-en-6-one (85828-15-5)

Guidance literature:

With hydrogen fluoride; In water; acetonitrile; for 1h; Ambient temperature;

DOI:10.1021/ja00304a031

Reference yield:

(1S,2S,3R,4R)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-(4,5-dimethyl-furan-2-yl)-2,4-dimethyl-pentan-1-ol (85828-13-3) → (1R,3S,4S,5R)-3-((S)-2-Benzyloxy-1-methyl-ethyl)-1,4,8-trimethyl-2,9-dioxa-bicyclo[3.3.1]non-7-en-6-one (85828-15-5)

Guidance literature:

With hydrogen fluoride; 3-chloro-benzenecarboperoxoic acid; Yield given. Multistep reaction; 1.) CH₂Cl₂, 0 deg C, 2.) CH₃CN, room temp.;

DOI:10.1021/jo00160a044

Reference yield:

2,3-dimethylfuran (14920-89-9) → (1R,3S,4S,5R)-3-((S)-2-Benzyloxy-1-methyl-ethyl)-1,4,8-trimethyl-2,9-dioxa-bicyclo[3.3.1]non-7-en-6-one (85828-15-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) t-BuLi / 1.) ether, 0 deg C, 2.) ether, -78 deg C

2: 1.) m-chloroperbenzoic acid, 2.) 5percent aq. HF / 1.) CH₂Cl₂, 0 deg C, 2.) CH₃CN, room temp.

With hydrogen fluoride; tert.-butyl lithium; 3-chloro-benzenecarboperoxoic acid;

DOI:10.1021/jo00160a044

upstream raw materials:

(1S,2S,3R,4R)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-(4,5-dimethyl-furan-2-yl)-2,4-dimethyl-pentan-1-ol

2,3-dimethylfuran

(2R,3S,4S)-1-Benzyloxy-2,4-dimethyl-hex-5-en-3-ol

(2S,3S,4S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentanal

Downstream raw materials:

<1R*-<1β,2α,4α,6β,7α,8β(1E,2E,4E,6R*)>>-1-(2,4-dimethoxybenzyl)-3-<1-hydroxy-4-methyl-6-(1,2,7-trimethyl-5-oxo-3,9,10-trioxatricyclo<4.3.1.0(2,4)>dec-8-yl)-2,4-heptadienylidene>-2,4-pyrrolidinedione