phenyl 3-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: phenyl 3-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside
• CAS No.: 128848-51-1
• Molecular Formula: C₂₆H₂₆O₅S
• Molecular Weight: 450.555
• Mol file: 128848-51-1.mol

Synonyms:phenyl 3-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside

Chemical Property of phenyl 3-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 3-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside

There total 19 articles about phenyl 3-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside 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: 98.0%

4-Acetoxy-2,2-dimethyl-butyric acid (2R,4aR,6S,7R,8S,8aR)-8-benzyloxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester → phenyl 3-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside (128848-51-1)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; at 20 ℃; for 3h;

DOI:10.1016/j.tetlet.2005.03.099

Reference yield: 93.0%

(2R,4aR,6S,7R,8R,8aS)-2-Phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol (71676-30-7,87508-18-7,138922-03-9,87508-17-6) + benzyl bromide (100-39-0) → phenyl 3-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside (128848-51-1)

Guidance literature:

(2R,4aR,6S,7R,8R,8aS)-2-Phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol; With di(n-butyl)tin oxide; In toluene; at 0 ℃; for 12h; Reflux;

benzyl bromide; With cesium fluoride; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 3h;

DOI:10.1021/acs.orglett.0c02692

Reference yield: 82.0%

benzaldehyde dimethyl acetal (1125-88-8) + phenyl 3-O-benzyl-1-thio-β-D-glucopyranoside (189144-54-5) → phenyl 3-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside (128848-51-1)

Guidance literature:

With toluene-4-sulfonic acid; In acetonitrile; at 20 ℃; for 3h;

DOI:10.1081/SCC-120027259

upstream raw materials:

(2R,4aR,6S,7R,8R,8aS)-2-Phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

benzyl bromide

benzaldehyde dimethyl acetal

phenyl 3-O-benzyl-1-thio-β-D-glucopyranoside

Downstream raw materials:

phenyl 3-O-benzyl-4,6-O-benzylidene-2-O-trimethylsilyl-1-thio-β-D-glucopyranoside

phenyl 3-O-benzyl-4,6-O-benzylidene-2-O-phenoxythiocarbonyl-1-thio-β-D-glucopyranoside

phenyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

phenyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside