methyl 2,3,6-tri-O-benzyl-4-O-(2,7-anhydro-6-deoxy-3-O-methyl-5-C-vinyl-β-D-manno-heptopyranosyl)-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 2,3,6-tri-O-benzyl-4-O-(2,7-anhydro-6-deoxy-3-O-methyl-5-C-vinyl-β-D-manno-heptopyranosyl)-α-D-glucopyranoside
• CAS No.: 507485-63-4
• Molecular Formula: C₃₈H₄₆O₁₀
• Molecular Weight: 662.777

Synonyms:methyl 2,3,6-tri-O-benzyl-4-O-(2,7-anhydro-6-deoxy-3-O-methyl-5-C-vinyl-β-D-manno-heptopyranosyl)-α-D-glucopyranoside

Chemical Property of methyl 2,3,6-tri-O-benzyl-4-O-(2,7-anhydro-6-deoxy-3-O-methyl-5-C-vinyl-β-D-manno-heptopyranosyl)-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-(2,7-anhydro-6-deoxy-3-O-methyl-5-C-vinyl-β-D-manno-heptopyranosyl)-α-D-glucopyranoside

There total 10 articles about methyl 2,3,6-tri-O-benzyl-4-O-(2,7-anhydro-6-deoxy-3-O-methyl-5-C-vinyl-β-D-manno-heptopyranosyl)-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: 84.0%

methyl 2,3,6-tri-O-benzyl-4-O-(2,7-anhydro-6-deoxy-3-O-methyl-4-O-tetrahydropyranyl-5-C-vinyl-β-D-manno-heptopyranosyl)-α-D-glucopyranoside (507485-62-3) → methyl 2,3,6-tri-O-benzyl-4-O-(2,7-anhydro-6-deoxy-3-O-methyl-5-C-vinyl-β-D-manno-heptopyranosyl)-α-D-glucopyranoside (507485-63-4)

Guidance literature:

With o-toluenesulfonic acid; In methanol; at 20 ℃; for 0.25h;

DOI:10.1002/1099-0690(200211)2002:21<3595::AID-EJOC3595>3.0.CO;2-F

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-(2,7-anhydro-6-deoxy-3-O-methyl-5-C-vinyl-β-D-manno-heptopyranosyl)-α-D-glucopyranoside (507485-63-4)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 80 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂

2.1: sodium / methanol / 8 h / 20 °C

2.2: p-toluenesulfonic acid / acetone / 20 °C

3.1: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂

4.1: lithium triethylborohydride / tetrahydrofuran

5.1: pyridine / 20 °C

6.1: 342.7 mg / acetic acid / 2 h / 60 °C

7.1: 91 percent / triethylamine; dimethylaminopyridine / CH₂Cl₂ / 20 °C

8.1: 93 percent / camphorsulfonic acid / CH₂Cl₂ / 0.33 h / 0 °C

9.1: NaOH / ethanol / 72 h

10.1: 84 percent / toluenesulfonic acid / methanol / 0.25 h / 20 °C

With pyridine; dmap; sodium hydroxide; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; o-toluenesulfonic acid; camphor-10-sulfonic acid; sodium; lithium triethylborohydride; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane;

DOI:10.1002/1099-0690(200211)2002:21<3595::AID-EJOC3595>3.0.CO;2-F

Reference yield:

methyl 2,3,6-tri-O-benzyl-4-O-(4,7-O-isopropylidene-6-deoxy-3-O-methyl-5-C-vinyl-β-D-gluco-heptopyranosyl)-α-D-glucopyranoside (507485-53-2) → methyl 2,3,6-tri-O-benzyl-4-O-(2,7-anhydro-6-deoxy-3-O-methyl-5-C-vinyl-β-D-manno-heptopyranosyl)-α-D-glucopyranoside (507485-63-4)

Guidance literature:

Multi-step reaction with 8 steps

1: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂

2: lithium triethylborohydride / tetrahydrofuran

3: pyridine / 20 °C

4: 342.7 mg / acetic acid / 2 h / 60 °C

5: 91 percent / triethylamine; dimethylaminopyridine / CH₂Cl₂ / 20 °C

6: 93 percent / camphorsulfonic acid / CH₂Cl₂ / 0.33 h / 0 °C

7: NaOH / ethanol / 72 h

8: 84 percent / toluenesulfonic acid / methanol / 0.25 h / 20 °C

With pyridine; dmap; sodium hydroxide; oxalyl dichloride; o-toluenesulfonic acid; camphor-10-sulfonic acid; lithium triethylborohydride; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane;

DOI:10.1002/1099-0690(200211)2002:21<3595::AID-EJOC3595>3.0.CO;2-F

upstream raw materials:

methyl 2,3,6-tri-O-benzyl-4-O-(2,7-anhydro-6-deoxy-3-O-methyl-4-O-tetrahydropyranyl-5-C-vinyl-β-D-manno-heptopyranosyl)-α-D-glucopyranoside

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

(2R,3S,4R,4aS,9aS)-2-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-4-methoxy-6,6-dimethyl-9a-vinyl-hexahydro-1,5,7-trioxa-benzocyclohepten-3-ol

methyl 2,3,6-tri-O-benzyl-4-O-(4,7-O-isopropylidene-6-deoxy-3-O-methyl-5-C-vinyl-β-D-gluco-heptopyranosyl)-α-D-glucopyranoside

Downstream raw materials:

methyl 2,3,6-tri-O-benzyl-4-O-(2,7-anhydro-5-C-benzyloxycarbonyl-3-O-methyl-β-D-manno-heptopyranosyl)-α-D-glucopyranoside

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