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

Base Information

• Chemical Name: (2S,3S,4R,5R,6R)-2,3-bis-benzyloxy-5-(3,4,5-trisbenzyloxy-6-benzyloxymethyltetrahydropyran-2-yl)benzoic acid methyl ester
• CAS No.: 1056028-66-0
• Molecular Formula: C₅₆H₅₄O₉
• Molecular Weight: 871.039
• Mol file: 1056028-66-0.mol

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

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

There total 14 articles about (2S,3S,4R,5R,6R)-2,3-bis-benzyloxy-5-(3,4,5-trisbenzyloxy-6-benzyloxymethyltetrahydropyran-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: 83.0%

1-C-[2,3-Bis(benzyloxy)-5-methoxycarbonylphenyl]-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose → (2S,3S,4R,5R,6R)-2,3-bis-benzyloxy-5-(3,4,5-trisbenzyloxy-6-benzyloxymethyltetrahydropyran-2-yl)benzoic acid methyl ester (1056028-66-0)

Guidance literature:

With chlorotriisopropylsilane; boron trifluoride diethyl etherate; In dichloromethane; acetonitrile; at -40 - 20 ℃; for 2h;

DOI:10.1016/j.tetlet.2015.01.054

Reference yield: 77.0%

(2,3,4,6-tetra-O-benzyl-2-β-D-glucopyranosyl)tri-n-butylstannane + methyl 2,3-bis(benzyloxy)-5-bromobenzoate (182676-91-1) → (2S,3S,4R,5R,6R)-2,3-bis-benzyloxy-5-(3,4,5-trisbenzyloxy-6-benzyloxymethyltetrahydropyran-2-yl)benzoic acid methyl ester (1056028-66-0)

Guidance literature:

With potassium fluoride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; bis(3,5-bis(trifluoromethyl)phenyl)(2’,4’,6’-triisopropyl-3,6-dimethoxy-[1,1’-biphenyl]-2-yl)phosphine; copper(l) chloride; In 1,4-dioxane; at 110 ℃; for 72h; Inert atmosphere;

DOI:10.1021/jacs.7b08707

Reference yield:

C27H28O9 + benzyl bromide (100-39-0) → (2S,3S,4R,5R,6R)-2,3-bis-benzyloxy-5-(3,4,5-trisbenzyloxy-6-benzyloxymethyltetrahydropyran-2-yl)benzoic acid methyl ester (1056028-66-0) + benzyloxy-5-benzyloxy-β-D-glucosyl-3,4-benzyloxysalicylate (1175558-87-8)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 25 ℃; for 15h; optical yield given as %de;

DOI:10.1021/ja8041564

upstream raw materials:

benzyl bromide

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

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

methyl 2,3-bis(benzyloxy)-5-bromobenzoate

Downstream raw materials:

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