1,6-anhydro-2,3-di-O-methyl-4-O-benzyl-5-C-phenyoxythiocarbonyloxy-β-L-idopyranose

Base Information

• Chemical Name: 1,6-anhydro-2,3-di-O-methyl-4-O-benzyl-5-C-phenyoxythiocarbonyloxy-β-L-idopyranose
• CAS No.: 1384974-94-0
• Molecular Formula: C₂₂H₂₄O₇S
• Molecular Weight: 432.494

Synonyms:1,6-anhydro-2,3-di-O-methyl-4-O-benzyl-5-C-phenyoxythiocarbonyloxy-β-L-idopyranose

Chemical Property of 1,6-anhydro-2,3-di-O-methyl-4-O-benzyl-5-C-phenyoxythiocarbonyloxy-β-L-idopyranose

Chemical Property:

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Technology Process of 1,6-anhydro-2,3-di-O-methyl-4-O-benzyl-5-C-phenyoxythiocarbonyloxy-β-L-idopyranose

There total 5 articles about 1,6-anhydro-2,3-di-O-methyl-4-O-benzyl-5-C-phenyoxythiocarbonyloxy-β-L-idopyranose 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: 60.0%

1,6-anhydro-2,3-di-O-methyl-5-C-hydroxy-4-O-benzyl-β-L-idopyranose (1384974-88-2) + phenylcarbonochloridothioate (1005-56-7) → 1,6-anhydro-2,3-di-O-methyl-4-O-benzyl-5-C-phenyoxythiocarbonyloxy-β-L-idopyranose (1384974-94-0)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 30h; Inert atmosphere;

DOI:10.1016/j.carres.2012.02.026

Reference yield: 39.0%

1,6-anhydro-2,3-di-O-methyl-5-C-hydroxy-4-O-benzyl-β-L-idopyranose (1384974-88-2) + phenylcarbonochloridothioate (1005-56-7) → (4S,5S,6R,7R)-4-benzyloxy-7-chloro-5,6-dimethoxyoxepan-3-one (1384974-95-1) + 1,6-anhydro-2,3-di-O-methyl-5-C-phenoxycarbonate-4-O-benzyl-β-L-idopyranose (1384974-93-9) + 1,6-anhydro-2,3-di-O-methyl-4-O-benzyl-5-C-phenyoxythiocarbonyloxy-β-L-idopyranose (1384974-94-0)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 20 ℃; for 20h; Inert atmosphere;

DOI:10.1016/j.carres.2012.02.026

Reference yield:

1,6-anhydro-2,3-di-O-methyl-5-C-hydroxy-4-O-benzyl-β-L-idopyranose (1384974-88-2) → 1,6-anhydro-2,3-di-O-methyl-4-O-benzyl-5-C-phenyoxythiocarbonyloxy-β-L-idopyranose (1384974-94-0)

Guidance literature:

Multi-step reaction with 3 steps

1: dmap / acetonitrile / 0.5 h / 85 °C / Microwave irradiation

2: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / Reflux

3: dmap; triethylamine / dichloromethane / 30 h / Inert atmosphere

With dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; triethylamine; In dichloromethane; toluene; acetonitrile;

DOI:10.1016/j.carres.2012.02.026

upstream raw materials:

C₁₉H₂₂N₂O₆S

1,6-anhydro-2,3-di-O-methyl-5-C-hydroxy-4-O-benzyl-β-L-idopyranose

phenylcarbonochloridothioate

Downstream raw materials:

(4S,5R,6S)-4-benzyloxy-5,6-dimethoxyoxepan-3-one

1,5-anhydro-2,3-di-O-methyl-4-O-benzyl-D-glucitol

6-O-acetyl-1,5-anhydro-2,3-di-O-methyl-4-O-benzyl-D-glucitol

1,6-di-O-acetyl-2,3-di-O-methyl-5-C-methoxy-4-O-benzyl-β-L-idopyranose

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