(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
• Mol file: 155346-00-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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%

(1S,2R,3S,5S)-7,7-dimethyl-4,6,8-trioxa-3-[(phenylmethoxy)methyl]bicyclo[3.3.0]octan-2-ol (155345-99-6) → (1R,3S,5S)-7,7-dimethyl-4,6,8-trioxa-3-[(phenylmethoxy)methyl]bicyclo[3.3.0]octan-2-one (155346-00-2)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 3.5h;

DOI:10.1080/15257770008033005

Reference yield:

benzyl bromide (100-39-0) → (1R,3S,5S)-7,7-dimethyl-4,6,8-trioxa-3-[(phenylmethoxy)methyl]bicyclo[3.3.0]octan-2-one (155346-00-2)

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:

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

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

upstream raw materials:

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

benzyl bromide

L-xylopyranose

6-hydroxy-2,2-dimethyl-5-(4-methylphenylsulfonyloxymethyl)-(3aS,5S,6R,6aS)-perhydrofuro[2,3-d][1,3]dioxole

Downstream raw materials:

1,2-O-(1-methylethylidene)-3-deoxy-3-methylene-5-O-benzyl-L-xylofuranose

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

1,2-O-(1-methylethylidene)-3-deoxy-3-(hydroxymethyl)-5-O-benzyl-L-ribofuranose

(1S,5S,7S,8S)-3,3-dimethyl-2,4,6-trioxa-7-[(phenylmethoxy)methyl]spiro[bicyclo[3.3.0]octane-8,5'-oxolane]-10-one