Benzyl 2,3,6-Tri-O-benzyl-4-C-(methyl)-α-D-glucopyranoside

Base Information

• Chemical Name: Benzyl 2,3,6-Tri-O-benzyl-4-C-(methyl)-α-D-glucopyranoside
• CAS No.: 139070-97-6
• Molecular Formula: C₃₅H₃₈O₆
• Molecular Weight: 554.683
• Mol file: 139070-97-6.mol

Synonyms:Benzyl 2,3,6-Tri-O-benzyl-4-C-(methyl)-α-D-glucopyranoside

Chemical Property of Benzyl 2,3,6-Tri-O-benzyl-4-C-(methyl)-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzyl 2,3,6-Tri-O-benzyl-4-C-(methyl)-α-D-glucopyranoside

There total 4 articles about Benzyl 2,3,6-Tri-O-benzyl-4-C-(methyl)-α-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: 80.0%

benzyl 4,41-anhydro-2,3,6-tri-O-benzyl-4-C-hydroxymethyl-α-D-glucopyranoside (146235-14-5) → Benzyl 2,3,6-Tri-O-benzyl-4-C-(methyl)-α-D-glucopyranoside (139070-97-6)

Guidance literature:

With hydrogen; Lindlar's catalyst; In methanol; ethyl acetate; for 16h;

DOI:10.1016/0008-6215(92)80085-F

Reference yield:

benzyl 2,3,6-tri-O-benzyl-4-deoxy-4-C-(methylene)-α-D-xylo-4-hexopyranoside (125219-21-8) → Benzyl 2,3,6-Tri-O-benzyl-4-C-(methyl)-α-D-glucopyranoside (139070-97-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 3-chloroperoxybenzoic acid / CH₂Cl₂ / 16 h / Ambient temperature

2: 80 percent / H₂ / palladium-on-calcium carbonate / ethyl acetate; methanol / 16 h

With hydrogen; 3-chloro-benzenecarboperoxoic acid; Lindlar's catalyst; In methanol; dichloromethane; ethyl acetate;

DOI:10.1016/0008-6215(92)80085-F

Reference yield:

benzyl 1,2,3,6-tetra-O-benzyl-α-D-glucopyranoside (58527-89-2) → Benzyl 2,3,6-Tri-O-benzyl-4-C-(methyl)-α-D-glucopyranoside (139070-97-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) dicyclohexylcarbodiimide, dimethyl sulfoxide, pyridine, CF₃CO₂H, 2) oxalic acid dihydrate / 1) Et₂O, 0 deg C, 2 h, 2) rt, 1 h

2: 1) n-butyllithium / 1) Et₂O, THF, -40 deg C, 1 h, 2) THF, -40 deg C, 30 min, then -5 deg C, 15 h

3: 1) borane-dimethylsulfide complex, 2) aq. NaOH, 30percent H₂O₂ / 1) THF, 5 deg C, 12 h, 2) 0 deg C, 1 h, then rt, 30 min

With pyridine; sodium hydroxide; n-butyllithium; dimethylsulfide borane complex; dihydrogen peroxide; oxalic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid;

upstream raw materials:

benzyl 2,3,6-tri-O-benzyl-4-deoxy-4-C-(methylene)-α-D-xylo-4-hexopyranoside

benzyl 4,4¹-anhydro-2,3,6-tri-O-benzyl-4-C-hydroxymethyl-α-D-glucopyranoside

benzyl 1,2,3,6-tetra-O-benzyl-α-D-glucopyranoside