octyl 6-O-(6-O-allyl-3,4-di-O-benzyl-α-D-mannopyranosyl)-2,3,4-tri-O-benzyl-β-D-glucopyranoside

Base Information

• Chemical Name: octyl 6-O-(6-O-allyl-3,4-di-O-benzyl-α-D-mannopyranosyl)-2,3,4-tri-O-benzyl-β-D-glucopyranoside
• CAS No.: 152157-64-7
• Molecular Formula: C₅₈H₇₂O₁₁
• Molecular Weight: 945.203
• Mol file: 152157-64-7.mol

Synonyms:octyl 6-O-(6-O-allyl-3,4-di-O-benzyl-α-D-mannopyranosyl)-2,3,4-tri-O-benzyl-β-D-glucopyranoside

Chemical Property of octyl 6-O-(6-O-allyl-3,4-di-O-benzyl-α-D-mannopyranosyl)-2,3,4-tri-O-benzyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of octyl 6-O-(6-O-allyl-3,4-di-O-benzyl-α-D-mannopyranosyl)-2,3,4-tri-O-benzyl-β-D-glucopyranoside

There total 5 articles about octyl 6-O-(6-O-allyl-3,4-di-O-benzyl-α-D-mannopyranosyl)-2,3,4-tri-O-benzyl-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: 96.0%

octyl 6-O-(2-O-acetyl-6-O-allyl-3,4-di-O-benzyl-α-D-mannopyranosyl)-2,3,4-tri-O-benzyl-β-D-glucopyranoside (152157-71-6) → octyl 6-O-(6-O-allyl-3,4-di-O-benzyl-α-D-mannopyranosyl)-2,3,4-tri-O-benzyl-β-D-glucopyranoside (152157-64-7)

Guidance literature:

With methanol; sodium methylate; for 6h; Ambient temperature;

DOI:10.1016/0008-6215(93)84087-M

Reference yield:

6-O-acetyl-3,4-di-O-benzyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose (79218-90-9) → octyl 6-O-(6-O-allyl-3,4-di-O-benzyl-α-D-mannopyranosyl)-2,3,4-tri-O-benzyl-β-D-glucopyranoside (152157-64-7)

Guidance literature:

Multi-step reaction with 5 steps

1: NaOMe, MeOH / 1 h

2: 1.) NaH / 1.) DMF, 30 min, 2.) room temperature, 14 h

3: Me₃SiCl / CH₂Cl₂ / 0.17 h / 5 °C

4: silver trifluoromethanesulfonate, N,N,N',N'-tetramethylurea, 4 Angstroem molecular sieves / CH₂Cl₂ / 14 h / Ambient temperature

5: 96 percent / NaOMe, MeOH / 6 h / Ambient temperature

With methanol; chloro-trimethyl-silane; 4 A molecular sieve; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; tetramethylurea; In dichloromethane;

DOI:10.1016/0008-6215(93)84087-M

Reference yield:

3,4-di-O-benzyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranoside (152174-59-9) → octyl 6-O-(6-O-allyl-3,4-di-O-benzyl-α-D-mannopyranosyl)-2,3,4-tri-O-benzyl-β-D-glucopyranoside (152157-64-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) NaH / 1.) DMF, 30 min, 2.) room temperature, 14 h

2: Me₃SiCl / CH₂Cl₂ / 0.17 h / 5 °C

3: silver trifluoromethanesulfonate, N,N,N',N'-tetramethylurea, 4 Angstroem molecular sieves / CH₂Cl₂ / 14 h / Ambient temperature

4: 96 percent / NaOMe, MeOH / 6 h / Ambient temperature

With methanol; chloro-trimethyl-silane; 4 A molecular sieve; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; tetramethylurea; In dichloromethane;

DOI:10.1016/0008-6215(93)84087-M

upstream raw materials:

octyl 6-O-(2-O-acetyl-6-O-allyl-3,4-di-O-benzyl-α-D-mannopyranosyl)-2,3,4-tri-O-benzyl-β-D-glucopyranoside

6-O-acetyl-3,4-di-O-benzyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose

3,4-di-O-benzyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranoside

Acetic acid (3S,4S,5R,6R)-6-allyloxymethyl-4,5-bis-benzyloxy-2-chloro-tetrahydro-pyran-3-yl ester