allyl-O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

Base Information

• Chemical Name: allyl-O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• CAS No.: 113842-90-3
• Molecular Formula: C₅₉H₆₄O₁₂
• Molecular Weight: 965.15
• Mol file: 113842-90-3.mol

Synonyms:allyl-O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

Chemical Property of allyl-O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl-O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

There total 8 articles about allyl-O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3,6-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: 100.0%

acetic anhydride (108-24-7) + allyl O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1<*>4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (113879-86-0) → allyl-O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (113842-90-3)

Guidance literature:

With pyridine; at 20 ℃; for 4h;

DOI:10.1016/0008-6215(87)80136-2

Reference yield:

benzyl bromide (100-39-0) → allyl-O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (113842-90-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.)(Bu₃Sn)2O 2.) Bu₄NBr / 1.) toluene, reflux, 4h, 2.) toluene, 80-85 deg C, 24h

2: 100 percent / pyridine / 4 h / 20 °C

With pyridine; tetrabutylammomium bromide; bis(tri-n-butyltin)oxide;

DOI:10.1016/0008-6215(87)80136-2

Reference yield:

allyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1<*>4)-2,3,6-tri-O-acetyl-β-D-gluco-pyranoside (97777-13-4) → allyl-O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (113842-90-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 3.3 g / 0.5M NaOMe / methanol / 2 h / 20 °C

2: 2.3 g / p-TsOH*H₂O / dimethylformamide / 1 h / 20 °C

3: 1.) 50percent NaH in oil / 1.DMF, 20 deg C, 30 min 2.) DMF, 1h

4: 70 percent / AcOH / methanol / 1 h / 80 °C

5: 1.)(Bu₃Sn)2O 2.) Bu₄NBr / 1.) toluene, reflux, 4h, 2.) toluene, 80-85 deg C, 24h

6: 100 percent / pyridine / 4 h / 20 °C

With pyridine; tetrabutylammomium bromide; sodium methylate; sodium hydride; toluene-4-sulfonic acid; acetic acid; bis(tri-n-butyltin)oxide; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(87)80136-2

upstream raw materials:

acetic anhydride

allyl O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1<*>4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

benzyl bromide

allyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1<*>4)-2,3,6-tri-O-acetyl-β-D-gluco-pyranoside

Downstream raw materials:

O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-D-glucopyranose

Acetic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-((2R,3R,4S)-4,5-bis-benzyloxy-2-benzyloxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester

O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranosyl fluoride

Acetic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-fluoro-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester