(1S,2R,3R,4R,5S,6R)-3-Benzyloxy-2,4-dimethyl-8-oxa-bicyclo[3.2.1]octan-6-ol

Base Information

Chemical Name:(1S,2R,3R,4R,5S,6R)-3-Benzyloxy-2,4-dimethyl-8-oxa-bicyclo[3.2.1]octan-6-ol
CAS No.:171231-74-6
Molecular Formula:C₁₆H₂₂O₃
Molecular Weight:262.349
Hs Code.:

Synonyms:(1S,2R,3R,4R,5S,6R)-3-Benzyloxy-2,4-dimethyl-8-oxa-bicyclo[3.2.1]octan-6-ol

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Chemical Property of (1S,2R,3R,4R,5S,6R)-3-Benzyloxy-2,4-dimethyl-8-oxa-bicyclo[3.2.1]octan-6-ol

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Technology Process of (1S,2R,3R,4R,5S,6R)-3-Benzyloxy-2,4-dimethyl-8-oxa-bicyclo[3.2.1]octan-6-ol

There total 4 articles about (1S,2R,3R,4R,5S,6R)-3-Benzyloxy-2,4-dimethyl-8-oxa-bicyclo[3.2.1]octan-6-ol 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: 96.0%

: 96691-92-8
(1R,2R,3r,4S,5S)-3-(benzyloxy)-2,4-dimethyl-8-oxa-bicyclo[3.2.1]oct-6-ene

: 171231-74-6
(1S,2R,3R,4R,5S,6R)-3-Benzyloxy-2,4-dimethyl-8-oxa-bicyclo[3.2.1]octan-6-ol

Guidance literature:: (1R,2R,3r,4S,5S)-3-(benzyloxy)-2,4-dimethyl-8-oxa-bicyclo[3.2.1]oct-6-ene; With diisopinocampheylborane; at -23 ℃; for 24h;

With sodium hydroxide; dihydrogen peroxide; In water; at 20 ℃; for 6h;
DOI:10.1016/S0040-4039(01)00799-7

Reference yield:

: 49747-05-9
endo-2,endo-4-Dimethyl-8-oxabicyclo<3.2.1>oct-6-en-3-on

: 171231-74-6
(1S,2R,3R,4R,5S,6R)-3-Benzyloxy-2,4-dimethyl-8-oxa-bicyclo[3.2.1]octan-6-ol

Guidance literature:: Multi-step reaction with 3 steps

1: DIBAL-H / CH₂Cl₂ / 1 h / -10 °C

2: NaH / tetrahydrofuran / 6 h / 65 °C

3: 1.) (-)Ipc₂BH; 2.) 3N NaOH, 30percent H₂O₂ / 1.) -20 deg C, 24 h; 2.) 5 h

With sodium hydroxide; dihydrogen peroxide; sodium hydride; diisobutylaluminium hydride; diisopinocampheylborane; In tetrahydrofuran; dichloromethane;
DOI:10.1016/0040-4039(95)01571-X

Reference yield:

: 100-39-0
benzyl bromide

: 171231-74-6
(1S,2R,3R,4R,5S,6R)-3-Benzyloxy-2,4-dimethyl-8-oxa-bicyclo[3.2.1]octan-6-ol

Guidance literature:: Multi-step reaction with 2 steps

1: NaH / tetrahydrofuran / 6 h / 65 °C

2: 1.) (-)Ipc₂BH; 2.) 3N NaOH, 30percent H₂O₂ / 1.) -20 deg C, 24 h; 2.) 5 h

With sodium hydroxide; dihydrogen peroxide; sodium hydride; diisopinocampheylborane; In tetrahydrofuran;
DOI:10.1016/0040-4039(95)01571-X