Benzoic acid (2S,3R,4S,5R,6S)-2-iodomethyl-6-methoxy-4,5-bis-(toluene-4-sulfonyloxy)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2S,3R,4S,5R,6S)-2-iodomethyl-6-methoxy-4,5-bis-(toluene-4-sulfonyloxy)-tetrahydro-pyran-3-yl ester
• CAS No.: 116809-47-3
• Molecular Formula: C₂₈H₂₉IO₁₀S₂
• Molecular Weight: 716.569
• Mol file: 116809-47-3.mol

Synonyms:Benzoic acid (2S,3R,4S,5R,6S)-2-iodomethyl-6-methoxy-4,5-bis-(toluene-4-sulfonyloxy)-tetrahydro-pyran-3-yl ester

Chemical Property of Benzoic acid (2S,3R,4S,5R,6S)-2-iodomethyl-6-methoxy-4,5-bis-(toluene-4-sulfonyloxy)-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2S,3R,4S,5R,6S)-2-iodomethyl-6-methoxy-4,5-bis-(toluene-4-sulfonyloxy)-tetrahydro-pyran-3-yl ester

There total 1 articles about Benzoic acid (2S,3R,4S,5R,6S)-2-iodomethyl-6-methoxy-4,5-bis-(toluene-4-sulfonyloxy)-tetrahydro-pyran-3-yl 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:

methyl 2,3-di-O-p-toluenesulfonyl-4-O-benzoyl-6-bromo-6-deoxy-α-D-glucopyranoside (101155-76-4) → Benzoic acid (2S,3R,4S,5R,6S)-2-iodomethyl-6-methoxy-4,5-bis-(toluene-4-sulfonyloxy)-tetrahydro-pyran-3-yl ester (116809-47-3)

Guidance literature:

With sodium iodide; In acetone; for 16h; Heating;

DOI:10.1021/jo00265a033

Reference yield:

Benzoic acid (2S,3R,4S,5R,6S)-2-iodomethyl-6-methoxy-4,5-bis-(toluene-4-sulfonyloxy)-tetrahydro-pyran-3-yl ester (116809-47-3) → methyl 4-O-benzoyl-2,3-di-O-toluene-p-sulfonyl-6-deoxy-α-D-glucopyranoside (116809-48-4)

Guidance literature:

With hydrogen; sodium acetate; palladium on activated charcoal; In ethanol; water; ethyl acetate; for 16h; Yield given;

DOI:10.1021/jo00265a033

Reference yield:

Benzoic acid (2S,3R,4S,5R,6S)-2-iodomethyl-6-methoxy-4,5-bis-(toluene-4-sulfonyloxy)-tetrahydro-pyran-3-yl ester (116809-47-3) → methyl 3,4-anhydro-6-deoxy-2-(tolylsulfonyl)allopyranoside (116809-49-5)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOAc, hydrogen / palladium on carbon / ethyl acetate; ethanol; H₂O / 16 h

2: LiOH / dioxane; methanol; H₂O / 16 h

With lithium hydroxide; hydrogen; sodium acetate; palladium on activated charcoal; In 1,4-dioxane; methanol; ethanol; water; ethyl acetate;

DOI:10.1021/jo00265a033

upstream raw materials:

methyl 2,3-di-O-p-toluenesulfonyl-4-O-benzoyl-6-bromo-6-deoxy-α-D-glucopyranoside

Downstream raw materials:

methyl 4-O-benzoyl-2,3-di-O-toluene-p-sulfonyl-6-deoxy-α-D-glucopyranoside

methyl 3,4-anhydro-6-deoxy-2-(tolylsulfonyl)allopyranoside

(3R,4R,6R)-6-Methyl-tetrahydro-pyran-2,3,4-triol

methyl 2-O-p-toluenesulfonyl-4,6-dideoxy-α-D-ribo-hexopyranoside