(2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS No.: 75336-67-3
• Molecular Formula: C₅₆H₆₀O₁₂
• Molecular Weight: 925.085

Synonyms:(2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property of (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

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Technology Process of (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 7 articles about (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic 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: 93.0%

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside (53008-65-4,641635-63-4) + C53H47NO11 → C25H19NO5 + (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (75336-67-3)

Guidance literature:

With calcium sulfate; [Ag(MeCN)₂][B{C₆H₃(CF₃)₂-3,5}₄]; α,α,α-trifluorotoluene; chloro[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]gold(I); In cyclohexane; at -15 ℃; for 18h; stereoselective reaction;

DOI:10.1021/jacs.1c04584

Reference yield: 78.0%

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside (53008-65-4,641635-63-4) + (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-chloro-tetrahydro-pyran-2-carboxylic acid methyl ester (75336-64-0) → (2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (75336-69-5) + (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (75336-67-3)

Guidance literature:

With silver perchlorate; acetonitrile; Yields of byproduct given; -15 deg C, 40 min before addition of hydroxy compound, -15 deg C, 2d;

DOI:10.1016/S0040-4039(00)92735-7

Reference yield: 78.0%

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside (53008-65-4,641635-63-4) + methyl <2,3,4-tri-O-benzyl-α-D-glucopyranosyl chloride>uronate (75336-63-9) → (2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (75336-69-5) + (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (75336-67-3)

Guidance literature:

With silver perchlorate; acetonitrile; Yields of byproduct given; -15 deg C, 40 min before addition of hydroxy compound, -15 deg C, 2d;

DOI:10.1016/S0040-4039(00)92735-7

upstream raw materials:

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside

(2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-chloro-tetrahydro-pyran-2-carboxylic acid methyl ester

methyl <2,3,4-tri-O-benzyl-α-D-glucopyranosyl chloride>uronate

methyl 2,3,4-tri-O-benzyl-α-D-glucopyranuronate

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