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

Base Information

• Chemical Name: 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
• CAS No.: 202648-90-6
• Molecular Formula: C₄₆H₅₄O₁₄S
• Molecular Weight: 862.992
• Mol file: 202648-90-6.mol

Synonyms: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

Chemical Property of 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

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

There total 10 articles about 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 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: 80.0%

p-toluenesulfonyl chloride (98-59-9) + methyl 2,3,6-tri-O-Benzyl-4-O-(2-O-acetyl-3-O-methyl-5-C-vinyl-β-D-mannopyranosyl)-α-D-glucopyranoside (202648-89-3) → 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 (202648-90-6)

Guidance literature:

With pyridine; at 20 ℃; for 3h;

DOI:10.1002/1521-3773(20010504)40:9<1670::AID-ANIE16700>3.0.CO;2-Q DOI:10.1002/1521-3765(20011119)7:22<4821::AID-CHEM4821>3.0.CO;2-N

Reference yield:

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) → 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 (202648-90-6)

Guidance literature:

Multi-step reaction with 5 steps

1: (COCl)2; DMSO; NEt₃ / CH₂Cl₂ / 0.75 h / -78 °C

2: 1.0 g / LiEt₃BH / tetrahydrofuran / 1 h / 20 °C

3: pyridine / 3 h / 20 °C

4: 660 mg / aq. AcOH / 2 h / 60 °C

5: 80 percent / pyridine / 3 h / 20 °C

With pyridine; oxalyl dichloride; lithium triethylborohydride; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 1: Swern oxidation;

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

Reference yield:

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-(2-O-acetyl-3-O-methyl-6-O-tosyl-5-C-vinyl-β-D-mannopyranosyl)-α-D-glucopyranoside (202648-90-6)

Guidance literature:

Multi-step reaction with 7 steps

1: Na; MeOH / 3 h / 20 °C

2: 1.7 g / p-TsOH / acetone / 16 h / 20 °C

3: (COCl)2; DMSO; NEt₃ / CH₂Cl₂ / 0.75 h / -78 °C

4: 1.0 g / LiEt₃BH / tetrahydrofuran / 1 h / 20 °C

5: pyridine / 3 h / 20 °C

6: 660 mg / aq. AcOH / 2 h / 60 °C

7: 80 percent / pyridine / 3 h / 20 °C

With pyridine; methanol; oxalyl dichloride; sodium; lithium triethylborohydride; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; acetone; 3: Swern oxidation;

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

upstream raw materials:

p-toluenesulfonyl chloride

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

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

methyl 2,3,6-tri-O-Benzyl-4-O-(4,6-O-isopropylidene-3-O-methyl-5-C-vinyl-β-D-mannopyranosyl)-α-D-gluco-pyranoside

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