methyl 7-O-allyl-2,3,4-tri-O-benzyl-D-glycero-α-D-gluco-heptopyranoside

Base Information

• Chemical Name: methyl 7-O-allyl-2,3,4-tri-O-benzyl-D-glycero-α-D-gluco-heptopyranoside
• CAS No.: 321142-22-7
• Molecular Formula: C₃₂H₃₈O₇
• Molecular Weight: 534.65
• Mol file: 321142-22-7.mol

Synonyms:methyl 7-O-allyl-2,3,4-tri-O-benzyl-D-glycero-α-D-gluco-heptopyranoside

Chemical Property of methyl 7-O-allyl-2,3,4-tri-O-benzyl-D-glycero-α-D-gluco-heptopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 7-O-allyl-2,3,4-tri-O-benzyl-D-glycero-α-D-gluco-heptopyranoside

There total 1 articles about methyl 7-O-allyl-2,3,4-tri-O-benzyl-D-glycero-α-D-gluco-heptopyranoside 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: 50.0%

methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside (83051-88-1) + allyl chloromethyl ether (3970-20-5) → methyl 7-O-allyl-2,3,4-tri-O-benzyl-D-glycero-α-D-gluco-heptopyranoside (321142-22-7) + methyl 7-O-allyl-2,3,4-tri-O-benzyl-L-glycero-α-D-gluco-heptopyranoside (321142-23-8)

Guidance literature:

allyl chloromethyl ether; With magnesium; mercury dichloride; In tetrahydrofuran; at -20 ℃; for 2h;

methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1016/S0040-4020(00)00847-4

Reference yield: 61.0%

methyl 7-O-allyl-2,3,4-tri-O-benzyl-D-glycero-α-D-gluco-heptopyranoside (321142-22-7) → methyl 2,3,4-tri-O-benzyl-D-glycero-α-D-gluco-heptopyranoside (103597-20-2)

Guidance literature:

methyl 7-O-allyl-2,3,4-tri-O-benzyl-D-glycero-α-D-gluco-heptopyranoside; With 1,4-diaza-bicyclo[2.2.2]octane; Wilkinson's catalyst; In ethanol; water; benzene; for 3h; Heating;

With mercury dichloride; mercury(II) oxide; In water; acetone; at 20 ℃; for 0.5h;

DOI:10.1016/S0040-4020(00)00847-4

Reference yield:

methyl 7-O-allyl-2,3,4-tri-O-benzyl-D-glycero-α-D-gluco-heptopyranoside (321142-22-7) → methyl 6,7-di-O-acetyl-2,3,4-tri-O-benzyl-D-glycero-α-D-gluco-heptopyranoside (103597-21-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1,4-diazabicyclo[2.2.2]octane; Rh(PPh₃)3Cl / ethanol; benzene; H₂O / 3 h / Heating

1.2: 61 percent / HgO; HgCl₂ / acetone; H₂O / 0.5 h / 20 °C

2.1: 92 percent / pyridine; DMAP

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; dmap; Wilkinson's catalyst; In ethanol; water; benzene;

DOI:10.1016/S0040-4020(00)00847-4

upstream raw materials:

methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside

allyl chloromethyl ether

Downstream raw materials:

methyl 2,3,4-tri-O-benzyl-D-glycero-α-D-gluco-heptopyranoside

methyl 6,7-di-O-acetyl-2,3,4-tri-O-benzyl-D-glycero-α-D-gluco-heptopyranoside