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

Base Information

• Chemical Name: methyl 2,3,6-tri-O-benzyl-4-O-(3-O-acetyl-2-O-methyl-5-C-vinyl-β-D-glucopyranosyl)-α-D-glucopyranoside
• CAS No.: 403725-05-3
• Molecular Formula: C₃₉H₄₈O₁₂
• Molecular Weight: 708.803

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

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

There total 14 articles about methyl 2,3,6-tri-O-benzyl-4-O-(3-O-acetyl-2-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:

Acetic acid (4aR,6R,7R,8S,8aS)-6-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-7-methoxy-2,2-dimethyl-4a-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester → methyl 2,3,6-tri-O-benzyl-4-O-(3-O-acetyl-2-O-methyl-5-C-vinyl-β-D-glucopyranosyl)-α-D-glucopyranoside (403725-05-3)

Guidance literature:

With acetic acid; at 70 ℃; for 1h;

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-(3-O-acetyl-2-O-methyl-5-C-vinyl-β-D-glucopyranosyl)-α-D-glucopyranoside (403725-05-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 78 percent / TMSOTf; molecular sieves / CH₂Cl₂ / 3 h / -78 - 20 °C

2: Na; MeOH / 6 h / 20 °C

3: 3.3 g / p-TsOH / acetone / 20 °C

4: 92 percent / NaH / dimethylformamide / 4 h / 20 °C

5: tBuOK / dimethylsulfoxide / 1 h / 80 °C

6: 1.83 g / HgO; aq. HgCl₂ / acetone / 1 h / 20 °C

7: pyridine / CH₂Cl₂ / 3 h / 20 °C

8: 1.0 g / aq. AcOH / 1 h / 70 °C

With pyridine; methanol; molecular sieve; trimethylsilyl trifluoromethanesulfonate; potassium tert-butylate; sodium; sodium hydride; toluene-4-sulfonic acid; acetic acid; mercury dichloride; mercury(II) oxide; In dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone;

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

Reference yield:

3-O-allyl-1,2-O-isopropylidene-α-D-glucofuranose (91882-92-7) → methyl 2,3,6-tri-O-benzyl-4-O-(3-O-acetyl-2-O-methyl-5-C-vinyl-β-D-glucopyranosyl)-α-D-glucopyranoside (403725-05-3)

Guidance literature:

Multi-step reaction with 13 steps

1: 95 percent / imidazole / CH₂Cl₂ / 4 h / 20 °C

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

3: 9.9 g / tetrahydrofuran / 1 h / 0 °C

4: IR-120 H(+) resin; H₂O / 8 h / 80 °C

5: 4.3 g / pyridine / 12 h / 20 °C

6: 78 percent / TMSOTf; molecular sieves / CH₂Cl₂ / 3 h / -78 - 20 °C

7: Na; MeOH / 6 h / 20 °C

8: 3.3 g / p-TsOH / acetone / 20 °C

9: 92 percent / NaH / dimethylformamide / 4 h / 20 °C

10: tBuOK / dimethylsulfoxide / 1 h / 80 °C

11: 1.83 g / HgO; aq. HgCl₂ / acetone / 1 h / 20 °C

12: pyridine / CH₂Cl₂ / 3 h / 20 °C

13: 1.0 g / aq. AcOH / 1 h / 70 °C

With pyridine; 1H-imidazole; methanol; molecular sieve; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; IR-120 H(+) resin; potassium tert-butylate; water; sodium; sodium hydride; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; 2: Swern oxidation / 3: Grignard reaction;

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

upstream raw materials:

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

3-O-allyl-1,2-O-isopropylidene-α-D-glucofuranose

3-O-allyl-6-O-(tert-butyldimethylsilyl)-5-oxo-1,2-O-isopropylidene-α-D-xylo-hexofuranose

(1R)-1-(3aR,5R,6S,6aR)-6-(allyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl-2-((tert-butyldimethylsilyl)oxy)ethanol

Downstream raw materials:

methyl 2,3,6-tri-O-benzyl-4-O-(3-O-5-C-methylene-2-O-methyl-5-C-vinyl-α-L-idopyranosyl)-α-D-glucopyranoside

methyl 2,3,6-tri-O-benzyl-4-O-(benzyl 2-O-methyl-3-O-5-C-methylene-α-L-idopyranosyluronate)-α-D-glucopyranoside

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

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