[(2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((Z)-styryl)-tetrahydro-pyran-3-yloxy]-acetic acid methyl ester

Base Information

• Chemical Name: [(2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((Z)-styryl)-tetrahydro-pyran-3-yloxy]-acetic acid methyl ester
• CAS No.: 695188-78-4
• Molecular Formula: C₃₈H₄₀O₇
• Molecular Weight: 608.731

Synonyms:[(2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((Z)-styryl)-tetrahydro-pyran-3-yloxy]-acetic acid methyl ester

Chemical Property of [(2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((Z)-styryl)-tetrahydro-pyran-3-yloxy]-acetic acid methyl ester

Chemical Property:

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Technology Process of [(2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((Z)-styryl)-tetrahydro-pyran-3-yloxy]-acetic acid methyl ester

There total 2 articles about [(2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((Z)-styryl)-tetrahydro-pyran-3-yloxy]-acetic 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: 95.0%

bromoacetic acid methyl ester (96-32-2) + 2-(3',4',6'-tri-O-benzyl-α-D-glucopyranosyl)-(Z)-styrene (135637-05-7) → [(2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((Z)-styryl)-tetrahydro-pyran-3-yloxy]-acetic acid methyl ester (695188-78-4)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; for 16h;

DOI:10.1002/ejoc.200600228

Reference yield: 72.0%

bromoacetic acid methyl ester (96-32-2) + 2-(3',4',6'-tri-O-benzyl-α-D-glucopyranosyl)-(Z)-styrene (135637-05-7) → trans-cyclopropane-1,2,3-tricarboxylic acid trimethyl ester (717-69-1) + [(2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((Z)-styryl)-tetrahydro-pyran-3-yloxy]-acetic acid methyl ester (695188-78-4)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; for 16h;

DOI:10.1055/s-2004-820021

Reference yield: 82.0%

[(2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((Z)-styryl)-tetrahydro-pyran-3-yloxy]-acetic acid methyl ester (695188-78-4) → (2R,3R,4R,5S,6R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-(2-methoxy-allyloxy)-6-((Z)-styryl)-tetrahydro-pyran (695188-80-8)

Guidance literature:

In tetrahydrofuran; at 60 ℃; for 48h;

DOI:10.1055/s-2004-820021

upstream raw materials:

bromoacetic acid methyl ester

2-(3',4',6'-tri-O-benzyl-α-D-glucopyranosyl)-(Z)-styrene

Downstream raw materials:

(2R,3R,4R,5S,6R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-(2-methoxy-allyloxy)-6-((Z)-styryl)-tetrahydro-pyran

(1R,6R,8S,9S,10S)-9,10-bis(benzyloxy)-8-benzyloxymethyl-4-methoxy-2,7-dioxabicyclo[4.4.0]dec-4-ene

(4aR,6R,7R,8R,8aS)-7,8-Bis-benzyloxy-6-benzyloxymethyl-octahydro-pyrano[3,2-b]pyran-3-ol

(1R,6R,8R,9S,10S)-9,10-bis(benzyloxy)-8-benzyloxymethyl-2,7-dioxabicyclo[4.4.0]decane-4-one

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