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

Base Information

• Chemical Name: (1S,2R,3S,5S)-7,7-dimethyl-4,6,8-trioxa-3-[(phenylmethoxy)methyl]bicyclo[3.3.0]octan-2-ol
• CAS No.: 155345-99-6
• Molecular Formula: C₁₅H₂₀O₅
• Molecular Weight: 280.321
• Mol file: 155345-99-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about (1S,2R,3S,5S)-7,7-dimethyl-4,6,8-trioxa-3-[(phenylmethoxy)methyl]bicyclo[3.3.0]octan-2-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: 98.4%

benzyl bromide (100-39-0) + 1,2-O-isopropylidene-α-L-xylofuranose (114861-22-2) → (1S,2R,3S,5S)-7,7-dimethyl-4,6,8-trioxa-3-[(phenylmethoxy)methyl]bicyclo[3.3.0]octan-2-ol (155345-99-6)

Guidance literature:

1,2-O-isopropylidene-α-L-xylofuranose; With bis(tri-n-butyltin)oxide; In toluene; for 5h; Heating;

benzyl bromide; With tetrabutylammomium bromide; In toluene; at 90 ℃; for 60h; Further stages.;

DOI:10.1021/jm9904607

Reference yield: 85.0%

sodium phenyl-methanolate (20194-18-7) + 6-hydroxy-2,2-dimethyl-5-(4-methylphenylsulfonyloxymethyl)-(3aS,5S,6R,6aS)-perhydrofuro[2,3-d][1,3]dioxole (218621-71-7) → (1S,2R,3S,5S)-7,7-dimethyl-4,6,8-trioxa-3-[(phenylmethoxy)methyl]bicyclo[3.3.0]octan-2-ol (155345-99-6)

Guidance literature:

at 100 ℃; for 17h;

DOI:10.1080/15257770008033005

Reference yield:

benzyl chloride (100-44-7) + 1,2-O-isopropylidene-α-L-xylofuranose (114861-22-2) → (1S,2R,3S,5S)-7,7-dimethyl-4,6,8-trioxa-3-[(phenylmethoxy)methyl]bicyclo[3.3.0]octan-2-ol (155345-99-6)

Guidance literature:

With pyridine; In dichloromethane; Inert atmosphere;

DOI:10.1021/jm900951n

upstream raw materials:

benzyl bromide

1,2-O-isopropylidene-α-L-xylofuranose

sodium phenyl-methanolate

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-(hydroxymethyl)-5-O-benzyl-L-ribofuranose

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

(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