methyl (allyl 2,3-di-O-benzyl-4-O-levulinoyl-α-D-glucopyranosid)uronate

Base Information

• Chemical Name: methyl (allyl 2,3-di-O-benzyl-4-O-levulinoyl-α-D-glucopyranosid)uronate
• CAS No.: 128564-05-6
• Molecular Formula: C₂₉H₃₄O₉
• Molecular Weight: 526.584
• Mol file: 128564-05-6.mol

Synonyms:methyl (allyl 2,3-di-O-benzyl-4-O-levulinoyl-α-D-glucopyranosid)uronate

Chemical Property of methyl (allyl 2,3-di-O-benzyl-4-O-levulinoyl-α-D-glucopyranosid)uronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (allyl 2,3-di-O-benzyl-4-O-levulinoyl-α-D-glucopyranosid)uronate

There total 6 articles about methyl (allyl 2,3-di-O-benzyl-4-O-levulinoyl-α-D-glucopyranosid)uronate 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:

methyl chloroformate (79-22-1) + (2S,3S,4S,5R,6S)-6-Allyloxy-4,5-bis-benzyloxy-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acid (126733-28-6) → methyl (allyl 2,3-di-O-benzyl-4-O-levulinoyl-α-D-glucopyranosid)uronate (128564-05-6)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 5 - 10 ℃; for 0.75h;

DOI:10.1002/hlca.19890720613

Reference yield:

levulinic anhydride (40608-06-8) → methyl (allyl 2,3-di-O-benzyl-4-O-levulinoyl-α-D-glucopyranosid)uronate (128564-05-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 4-(dimethylamino)pyridine / pyridine / 2 h / 0 °C

2: 95.75 g / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.75 h / 5 - 10 °C

With dmap; triethylamine; In pyridine; dichloromethane;

DOI:10.1002/hlca.19890720613

Reference yield:

allyl 2,3-di-O-benzyl-α-D-glucopyranoside (87326-32-7) → methyl (allyl 2,3-di-O-benzyl-4-O-levulinoyl-α-D-glucopyranosid)uronate (128564-05-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 2.) 4-(dimethylamino)pyridine / 1.) pyridine, 80 deg C, 3.5 h; 2.) pyridine, r.t., 19 h

2: CrO₃, H₂SO₄ / H₂O; acetone / 33 h / Ambient temperature

3: 95.75 g / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.75 h / 5 - 10 °C

With chromium(VI) oxide; dmap; sulfuric acid; triethylamine; In dichloromethane; water; acetone;

DOI:10.1002/hlca.19890720613

upstream raw materials:

methyl chloroformate

(2S,3S,4S,5R,6S)-6-Allyloxy-4,5-bis-benzyloxy-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acid

levulinic anhydride

allyl 2,3-di-O-benzyl-α-D-glucopyranoside

Downstream raw materials:

methyl 2,3-di-O-benzyl-4-O-levulinoyl-α-D-glucopyranuronate

methyl (prop-1-enyl 2,3-di-O-benzyl-4-O-levulinoyl-α-D-glucopyranosid)uronate