(2S,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-carboxylic acid

Base Information

• Chemical Name: (2S,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-carboxylic acid
• CAS No.: 120444-48-6
• Molecular Formula: C₂₈H₃₀O₇
• Molecular Weight: 478.542
• Mol file: 120444-48-6.mol

Synonyms:(2S,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-carboxylic acid

Chemical Property of (2S,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-carboxylic acid

There total 10 articles about (2S,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-carboxylic acid 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) → (2S,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-carboxylic acid (120444-48-6)

Guidance literature:

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; In dichloromethane; water;

DOI:10.1021/jo300986c

Reference yield: 80.0%

methyl 2,3,4-tri-O-benzyl-β-D-galactopyranoside (40653-32-5,641635-63-4) → (2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid (4356-82-5,67462-49-1,81369-73-5,120444-48-6)

Guidance literature:

With chromium(VI) oxide; sulfuric acid; In acetone;

DOI:10.1016/S0040-4039(00)86685-X

Reference yield: 10.0%

methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside (83051-88-1) → (2S,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-carboxylic acid (120444-48-6)

Guidance literature:

With 1-chloro-1λ³-benzo[d][1,2]iodaoxol-3(1H)-one; In dichloromethane; water; at 20 ℃; for 5h;

DOI:10.1016/j.tetlet.2018.05.021

upstream raw materials:

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

methyl (methyl-2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate

methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside

methyl 2,3,4-tri-O-benzyl-6-O-trityl-α-D-glucopyranoside

Downstream raw materials:

Methyl-(methyl-D-galactopyranosid) uronate, β anomer

methyl (methyl 2,3,4-tri-O-benzyl-β-D-galactopyranosid)uronate

(E)-(R)-3-((3aR,5R,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-1-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-prop-2-en-1-ol

(E)-3-((3aR,5R,6R,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-1-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propenone