(2R,3R,4S,5R,6R)-2-chloro-6-(benzoyloxymethyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate

Base Information

• Chemical Name: (2R,3R,4S,5R,6R)-2-chloro-6-(benzoyloxymethyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate
• CAS No.: 15067-04-6
• Molecular Formula: C₃₄H₂₇ClO₉
• Molecular Weight: 615.036

Synonyms:(2R,3R,4S,5R,6R)-2-chloro-6-(benzoyloxymethyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate

Chemical Property of (2R,3R,4S,5R,6R)-2-chloro-6-(benzoyloxymethyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate

Chemical Property:

Purity/Quality:

99%, ^*data from raw suppliers

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Technology Process of (2R,3R,4S,5R,6R)-2-chloro-6-(benzoyloxymethyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate

There total 8 articles about (2R,3R,4S,5R,6R)-2-chloro-6-(benzoyloxymethyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate 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: 85.0%

1,2,3,4,6-penta-O-benzoyl-D-glucopyranoside (2592-58-7,3006-48-2,3006-49-3,13526-09-5,14679-57-3,22415-91-4,29884-70-6,41545-55-5,41545-56-6,41569-33-9,96996-90-6,121570-85-2,121570-86-3) → (2R,3R,4S,5R,6R)-2-chloro-6-(benzoyloxymethyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate (15067-04-6)

Guidance literature:

With bismuth(III) oxychloride; thionyl chloride; In dichloromethane; at 20 ℃;

DOI:10.1016/j.tetlet.2004.10.138

Reference yield: 84.0%

2,3,4,6-tetra-O-benzoylglucosyl bromide (14218-11-2) + 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (4064-06-6) → (2R,3R,4S,5R,6R)-2-chloro-6-(benzoyloxymethyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate (15067-04-6) + 1,2:3:4-di-O-isopropylidene-6-O-(tetra-O-benzoyl-β-D-glucopyranosyl)-α-D-galactose (70751-54-1)

Guidance literature:

With zinc(II) chloride; In dichloromethane; at 20 ℃; for 48h;

DOI:10.1016/j.carres.2008.03.019

Reference yield: 81.0%

C40H44O5S → (2R,3R,4S,5R,6R)-2-chloro-6-(benzoyloxymethyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate (15067-04-6)

Guidance literature:

With Iodine monochloride; In dichloromethane; toluene; at 20 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

upstream raw materials:

1,2,3,4,6-penta-O-benzoyl-β-D-glucopyranose

1,2,3,4,6-penta-O-benzoyl-D-glucopyranoside

2,3,4,6-tetra-O-benzoylglucosyl bromide

1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

Downstream raw materials:

methyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

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