methyl 2,3,6-tri-O-benzyl-4-O-(4,6-O-isopropylidene-3-O-methyl-5-C-vinyl-β-D-glucopyranosyl)-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 2,3,6-tri-O-benzyl-4-O-(4,6-O-isopropylidene-3-O-methyl-5-C-vinyl-β-D-glucopyranosyl)-α-D-glucopyranoside
• CAS No.: 202649-52-3
• Molecular Formula: C₄₀H₅₀O₁₁
• Molecular Weight: 706.83
• Mol file: 202649-52-3.mol

Synonyms:methyl 2,3,6-tri-O-benzyl-4-O-(4,6-O-isopropylidene-3-O-methyl-5-C-vinyl-β-D-glucopyranosyl)-α-D-glucopyranoside

Chemical Property of methyl 2,3,6-tri-O-benzyl-4-O-(4,6-O-isopropylidene-3-O-methyl-5-C-vinyl-β-D-glucopyranosyl)-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,3,6-tri-O-benzyl-4-O-(4,6-O-isopropylidene-3-O-methyl-5-C-vinyl-β-D-glucopyranosyl)-α-D-glucopyranoside

There total 6 articles about methyl 2,3,6-tri-O-benzyl-4-O-(4,6-O-isopropylidene-3-O-methyl-5-C-vinyl-β-D-glucopyranosyl)-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: 70.0%

2,2-dimethoxy-propane (77-76-9) + methyl 2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-acetyl-3-O-methyl-5-C-vinyl-β-D-glucopyranosyl)-α-D-glucano-side (202648-85-9) → methyl 2,3,6-tri-O-benzyl-4-O-(4,6-O-isopropylidene-3-O-methyl-5-C-vinyl-β-D-glucopyranosyl)-α-D-glucopyranoside (202649-52-3)

Guidance literature:

methyl 2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-acetyl-3-O-methyl-5-C-vinyl-β-D-glucopyranosyl)-α-D-glucano-side; In methanol; at 0 - 20 ℃;

2,2-dimethoxy-propane; With toluene-4-sulfonic acid; In acetone; at 20 ℃; for 16h;

DOI:10.1002/1521-3773(20010504)40:9<1670::AID-ANIE16700>3.0.CO;2-Q

Reference yield:

2,2-dimethoxy-propane (77-76-9) + (2R,3S,4S,5R,6R)-6-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-hydroxymethyl-4-methoxy-2-vinyl-tetrahydro-pyran-3,5-diol (202648-86-0) → methyl 2,3,6-tri-O-benzyl-4-O-(4,6-O-isopropylidene-3-O-methyl-5-C-vinyl-β-D-glucopyranosyl)-α-D-glucopyranoside (202649-52-3)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; at 20 ℃; for 16h;

DOI:10.1002/1521-3765(20011119)7:22<4821::AID-CHEM4821>3.0.CO;2-N

Reference yield:

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside (19488-48-3) → methyl 2,3,6-tri-O-benzyl-4-O-(4,6-O-isopropylidene-3-O-methyl-5-C-vinyl-β-D-glucopyranosyl)-α-D-glucopyranoside (202649-52-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 85 percent / TMSOTf / CH₂Cl₂ / 2 h / -78 °C

2.1: MaONa / methanol / 0 - 20 °C

2.2: 70 percent / p-TsOH / acetone / 16 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; In methanol; dichloromethane;

DOI:10.1002/1521-3773(20010504)40:9<1670::AID-ANIE16700>3.0.CO;2-Q

upstream raw materials:

2,2-dimethoxy-propane

methyl 2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-acetyl-3-O-methyl-5-C-vinyl-β-D-glucopyranosyl)-α-D-glucano-side

(2R,3S,4S,5R,6R)-6-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-hydroxymethyl-4-methoxy-2-vinyl-tetrahydro-pyran-3,5-diol

1,2,4,6-tetra-O-acetyl-3-O-methyl-5-C-vinyl-β-D-gluco-pyranose

Downstream raw materials:

methyl 2,3,6-tri-O-Benzyl-4-O-(2,6-anhydro-3-O-methyl-5-C-vinyl-β-D-mannopyranosyl)-α-D-glucopyranoside

methyl 2,3,6-tri-O-Benzyl-4-O-(2-O-acetyl-3-O-methyl-5-C-vinyl-β-D-mannopyranosyl)-α-D-glucopyranoside

methyl 2,3,6-tri-O-benzyl-4-O-(2,6-anhydro-5-C-benzyloxycarbonyl-3-O-methyl-β-D-mannopyranosyl)-α-D-glucopyranoside

methyl 2,3,6-tri-O-benzyl-4-O-(2-O-acetyl-3-O-methyl-6-O-tosyl-5-C-vinyl-β-D-mannopyranosyl)-α-D-glucopyranoside