Acetic acid (2S,3S,4R,5R)-4-acetoxy-2-[(2R,3R,4S,5R,6R)-4,5-diacetoxy-3-(toluene-4-sulfonyloxy)-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-2-yloxy]-2,5-bis-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3S,4R,5R)-4-acetoxy-2-[(2R,3R,4S,5R,6R)-4,5-diacetoxy-3-(toluene-4-sulfonyloxy)-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-2-yloxy]-2,5-bis-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester
• CAS No.: 74801-18-6
• Molecular Formula: C₄₈H₅₄O₂₃S₄
• Molecular Weight: 1127.21

Synonyms:

Chemical Property of Acetic acid (2S,3S,4R,5R)-4-acetoxy-2-[(2R,3R,4S,5R,6R)-4,5-diacetoxy-3-(toluene-4-sulfonyloxy)-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-2-yloxy]-2,5-bis-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester

Chemical Property:

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Technology Process of Acetic acid (2S,3S,4R,5R)-4-acetoxy-2-[(2R,3R,4S,5R,6R)-4,5-diacetoxy-3-(toluene-4-sulfonyloxy)-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-2-yloxy]-2,5-bis-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester

There total 3 articles about Acetic acid (2S,3S,4R,5R)-4-acetoxy-2-[(2R,3R,4S,5R,6R)-4,5-diacetoxy-3-(toluene-4-sulfonyloxy)-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-2-yloxy]-2,5-bis-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-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: 85.0%

acetic anhydride (108-24-7) + 1’,2,6,6’-tetra-O-tosylsucrose (74801-17-5) → Acetic acid (2S,3S,4R,5R)-4-acetoxy-2-[(2R,3R,4S,5R,6R)-4,5-diacetoxy-3-(toluene-4-sulfonyloxy)-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-2-yloxy]-2,5-bis-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester (74801-18-6)

Guidance literature:

In pyridine;

DOI:10.1016/S0008-6215(00)85374-4

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → Acetic acid (2S,3S,4R,5R)-4-acetoxy-2-[(2R,3R,4S,5R,6R)-4,5-diacetoxy-3-(toluene-4-sulfonyloxy)-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-2-yloxy]-2,5-bis-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester (74801-18-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 32 percent / pyridine / 72 h / 0 °C

2: 85 percent / pyridine

In pyridine;

DOI:10.1016/S0008-6215(00)85374-4

Reference yield:

Sucrose (57-50-1) → Acetic acid (2S,3S,4R,5R)-4-acetoxy-2-[(2R,3R,4S,5R,6R)-4,5-diacetoxy-3-(toluene-4-sulfonyloxy)-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-2-yloxy]-2,5-bis-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester (74801-18-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 32 percent / pyridine / 72 h / 0 °C

2: 85 percent / pyridine

In pyridine;

DOI:10.1016/S0008-6215(00)85374-4

upstream raw materials:

acetic anhydride

1’,2,6,6’-tetra-O-tosylsucrose

p-toluenesulfonyl chloride

Sucrose

Downstream raw materials:

3,6:1',4':3,6'-trianhydro-2-O-tosylsucrose

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