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

Base Information

• Chemical Name: benzyl 2,3,6-tri-O-benzyl-4-deoxy-4-C-(methylene)-α-D-xylo-4-hexopyranoside
• CAS No.: 125219-21-8
• Molecular Formula: C₃₅H₃₆O₅
• Molecular Weight: 536.668
• Mol file: 125219-21-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about benzyl 2,3,6-tri-O-benzyl-4-deoxy-4-C-(methylene)-α-D-xylo-4-hexopyranoside 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: 75.0%

benzyl 2,3,6-tri-O-benzyl-α-D-xylo-hex-4-ulopyranoside (125219-26-3) + Methylenetriphenylphosphorane (19493-09-5) → benzyl 2,3,6-tri-O-benzyl-4-deoxy-4-C-(methylene)-α-D-xylo-4-hexopyranoside (125219-21-8)

Guidance literature:

Wittig methylenation;

DOI:10.1016/S0040-4039(00)99257-8

Reference yield: 68.0%

methyl-triphenylphosphonium iodide (2065-66-9) + benzyl 2,3,6-tri-O-benzyl-α-D-xylo-hex-4-ulopyranoside (125219-26-3) → benzyl 2,3,6-tri-O-benzyl-4-deoxy-4-C-(methylene)-α-D-xylo-4-hexopyranoside (125219-21-8)

Guidance literature:

methyl-triphenylphosphonium iodide; With n-butyllithium; In tetrahydrofuran; at 0 ℃; for 0.25h;

benzyl 2,3,6-tri-O-benzyl-α-D-xylo-hex-4-ulopyranoside; In tetrahydrofuran; for 2h;

DOI:10.1016/j.carres.2011.08.030

Reference yield:

benzyl 1,2,3,6-tetra-O-benzyl-α-D-glucopyranoside (58527-89-2) → benzyl 2,3,6-tri-O-benzyl-4-deoxy-4-C-(methylene)-α-D-xylo-4-hexopyranoside (125219-21-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 4.98 g / DMSO, (COCl)2 / CH₂Cl₂ / 0.5 h / -78 °C

2: 45 percent / toluene; tetrahydrofuran / 1.) -40 - 0 deg C, 1 h, 2.) 0 deg C, 16 h

With oxalyl dichloride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; toluene;

upstream raw materials:

Methyltriphenylphosphonium bromide

benzyl 2,3,6-tri-O-benzyl-α-D-xylo-hex-4-ulopyranoside

Methylenetriphenylphosphorane

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

Downstream raw materials:

(4-deoxy-4-methyl-(1,2,3,6-tetra-O-benzyl-α-D-glucopyranosyl))-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranoside

(4-deoxy-4-methyl-(1,2,3,6-tetra-O-benzyl-α-D-glucopyranosyl))-(2,3,4,6-tetra-O-acetyl)-β-D-galactopyranoside

(4-deoxy-4-methyl-(1,2,3,6-tetra-O-benzyl-α-D-glucopyranosyl))-(2,3,4,6-tetra-O-benzyl)-α-D-glucopyranoside

(S)-((4S,5R,6R)-3-Benzenesulfinyl-4,5-bis-benzyloxy-6-benzyloxymethyl-5,6-dihydro-4H-pyran-2-yl)-((2S,3R,4S,5R,6S)-4,5,6-tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yl)-methanol