(1R,3S,5S)-7,7-dimethyl-4,6,8-trioxa-3-[(phenylmethoxy)methyl]bicyclo[3.3.0]octan-2-one

Base Information

Chemical Name:(1R,3S,5S)-7,7-dimethyl-4,6,8-trioxa-3-[(phenylmethoxy)methyl]bicyclo[3.3.0]octan-2-one
CAS No.:155346-00-2
Molecular Formula:C₁₅H₁₈O₅
Molecular Weight:278.305
Hs Code.:

Synonyms:(1R,3S,5S)-7,7-dimethyl-4,6,8-trioxa-3-[(phenylmethoxy)methyl]bicyclo[3.3.0]octan-2-one

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Chemical Property of (1R,3S,5S)-7,7-dimethyl-4,6,8-trioxa-3-[(phenylmethoxy)methyl]bicyclo[3.3.0]octan-2-one

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Technology Process of (1R,3S,5S)-7,7-dimethyl-4,6,8-trioxa-3-[(phenylmethoxy)methyl]bicyclo[3.3.0]octan-2-one

There total 4 articles about (1R,3S,5S)-7,7-dimethyl-4,6,8-trioxa-3-[(phenylmethoxy)methyl]bicyclo[3.3.0]octan-2-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: 99.0%

: 155345-99-6
(1S,2R,3S,5S)-7,7-dimethyl-4,6,8-trioxa-3-[(phenylmethoxy)methyl]bicyclo[3.3.0]octan-2-ol

: 155346-00-2
(1R,3S,5S)-7,7-dimethyl-4,6,8-trioxa-3-[(phenylmethoxy)methyl]bicyclo[3.3.0]octan-2-one

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 3.5h;
DOI:10.1080/15257770008033005

Reference yield:

: 100-39-0
benzyl bromide

: 155346-00-2
(1R,3S,5S)-7,7-dimethyl-4,6,8-trioxa-3-[(phenylmethoxy)methyl]bicyclo[3.3.0]octan-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: bis(tributyltin) oxide / toluene / 5 h / Heating

1.2: 98.4 percent / tetrabutylammonium bromide / toluene / 60 h / 90 °C

2.1: 98 percent / pyridinium dichromate; acetic acid; molecular sieve 4A / CH₂Cl₂ / 1 h

With dipyridinium dichromate; 4 A molecular sieve; acetic acid; bis(tri-n-butyltin)oxide; In dichloromethane; toluene; 1.1: Condensation / 1.2: Alkylation / 2.1: Oxidation;
DOI:10.1021/jm9904607

Reference yield:

: 87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,36562-42-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2
L-xylopyranose

: 155346-00-2
(1R,3S,5S)-7,7-dimethyl-4,6,8-trioxa-3-[(phenylmethoxy)methyl]bicyclo[3.3.0]octan-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: CuSO₄; H₂SO₄ / acetone / 36 h / 20 °C

1.2: 98 percent / aq. HCl / H₂O / 6 h

2.1: 71 percent / pyridine / CHCl₃ / 20 °C

3.1: 85 percent / 17 h / 100 °C

4.1: 99 percent / dess-Martin periodinane / CH₂Cl₂ / 3.5 h / 20 °C

With pyridine; sulfuric acid; Dess-Martin periodane; copper(II) sulfate; In dichloromethane; chloroform; acetone; 1.1: Condensation / 1.2: Hydrolysis / 2.1: Tosylation / 3.1: Substitution / 4.1: Dess-Martin oxidation;
DOI:10.1080/15257770008033005