(2S,3S,4R,5R,6R)-2,3-bis-benzyloxy-5-(3,4,5-triacetoxy-6-acetoxymethyltetrahydropyran-2-yl)benzoic acid methyl ester

Base Information

• Chemical Name: (2S,3S,4R,5R,6R)-2,3-bis-benzyloxy-5-(3,4,5-triacetoxy-6-acetoxymethyltetrahydropyran-2-yl)benzoic acid methyl ester
• CAS No.: 1056028-65-9
• Molecular Formula: C₃₆H₃₈O₁₃
• Molecular Weight: 678.69
• Mol file: 1056028-65-9.mol

Synonyms:(2S,3S,4R,5R,6R)-2,3-bis-benzyloxy-5-(3,4,5-triacetoxy-6-acetoxymethyltetrahydropyran-2-yl)benzoic acid methyl ester

Chemical Property of (2S,3S,4R,5R,6R)-2,3-bis-benzyloxy-5-(3,4,5-triacetoxy-6-acetoxymethyltetrahydropyran-2-yl)benzoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R,5R,6R)-2,3-bis-benzyloxy-5-(3,4,5-triacetoxy-6-acetoxymethyltetrahydropyran-2-yl)benzoic acid methyl ester

There total 7 articles about (2S,3S,4R,5R,6R)-2,3-bis-benzyloxy-5-(3,4,5-triacetoxy-6-acetoxymethyltetrahydropyran-2-yl)benzoic acid methyl ester 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: 66.0%

2,3-bis-benzyloxy-5-iodobenzoic acid methyl ester (1056028-64-8) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → (2S,3S,4R,5R,6R)-2,3-bis-benzyloxy-5-(3,4,5-triacetoxy-6-acetoxymethyltetrahydropyran-2-yl)benzoic acid methyl ester (1056028-65-9)

Guidance literature:

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; lithium chloride; zinc; In N,N-dimethyl-formamide;

DOI:10.1016/j.jinorgbio.2018.10.008

Reference yield: 55.0%

C22H19IO4Zn*ClLi + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → (2S,3S,4R,5R,6R)-2,3-bis-benzyloxy-5-(3,4,5-triacetoxy-6-acetoxymethyltetrahydropyran-2-yl)benzoic acid methyl ester (1056028-65-9)

Guidance literature:

With bis (1,5-cyclopentadiene)nickel ⁽⁰⁾; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine; In N,N-dimethyl-formamide; at 25 ℃; for 12h; optical yield given as %de;

DOI:10.1021/ja8041564

Reference yield:

methyl 5-iodo-3-methoxysalicylate (134419-44-6) → (2S,3S,4R,5R,6R)-2,3-bis-benzyloxy-5-(3,4,5-triacetoxy-6-acetoxymethyltetrahydropyran-2-yl)benzoic acid methyl ester (1056028-65-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: boron tribromide / dichloromethane; water / 1 h / 20 °C / Inert atmosphere

1.2: Reflux

2.1: sodium iodide / N,N-dimethyl-formamide

3.1: lithium chloride; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; zinc / N,N-dimethyl-formamide

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; boron tribromide; sodium iodide; lithium chloride; zinc; In dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.jinorgbio.2018.10.008

upstream raw materials:

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

methyl 5-iodo-3-methoxysalicylate

2,3-dihydroxy-5-iodobenzoic acid methyl ester

2,3-bis-benzyloxy-5-iodobenzoic acid methyl ester

Downstream raw materials:

(2S,3S,4R,5R,6R)-2,3-bis-benzyloxy-5-(3,4,5-tris-benzyloxy-6-benzyloxymethyltetrahydropyran-2-yl)benzoic acid

(2S,3S,4R,5R,6R)-2,3-bis-benzyloxy-5-(3,4,5-trisbenzyloxy-6-benzyloxymethyltetrahydropyran-2-yl)benzoic acid methyl ester

benzyloxy-5-benzyloxy-β-D-glucosyl-3,4-benzyloxysalicylate