6-O-acetyl-2,3,4,2',3',4'-hexa-O-benzyl-6'-O-(methylsulfonyl)-α-α-trehalose

Base Information

• Chemical Name: 6-O-acetyl-2,3,4,2',3',4'-hexa-O-benzyl-6'-O-(methylsulfonyl)-α-α-trehalose
• CAS No.: 89421-64-7
• Molecular Formula: C₅₇H₆₂O₁₄S
• Molecular Weight: 1003.18
• Mol file: 89421-64-7.mol

Synonyms:6-O-acetyl-2,3,4,2',3',4'-hexa-O-benzyl-6'-O-(methylsulfonyl)-α-α-trehalose

Chemical Property of 6-O-acetyl-2,3,4,2',3',4'-hexa-O-benzyl-6'-O-(methylsulfonyl)-α-α-trehalose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-O-acetyl-2,3,4,2',3',4'-hexa-O-benzyl-6'-O-(methylsulfonyl)-α-α-trehalose

There total 2 articles about 6-O-acetyl-2,3,4,2',3',4'-hexa-O-benzyl-6'-O-(methylsulfonyl)-α-α-trehalose 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%

methanesulfonyl chloride (124-63-0) + 2,3,4,2',3',4'-hexa-(benzyloxy)-6-acetyloxy-α,α-trehalose (89401-23-0) → 6-O-acetyl-2,3,4,2',3',4'-hexa-O-benzyl-6'-O-(methylsulfonyl)-α-α-trehalose (89421-64-7)

Guidance literature:

In pyridine; 1.) 0 deg C, 30 min; rt, 2 h.;

DOI:10.1016/0008-6215(84)85168-X

Reference yield:

[(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl]-methanol (125177-97-1,128188-35-2,74501-33-0) → 6-O-acetyl-2,3,4,2',3',4'-hexa-O-benzyl-6'-O-(methylsulfonyl)-α-α-trehalose (89421-64-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 27 percent / H₂O / 18 h / 75 °C

2: 93 percent / pyridine / 1.) 0 deg C, 30 min; rt, 2 h.

In pyridine; water;

DOI:10.1016/0008-6215(84)85168-X

Reference yield: 79.0%

6-O-acetyl-2,3,4,2',3',4'-hexa-O-benzyl-6'-O-(methylsulfonyl)-α-α-trehalose (89421-64-7) → 2,3,4,2',3',4'-hexa-O-benzyl-6'-O-(methylsulfonyl)-α-α-trehalose (89401-24-1)

Guidance literature:

With sodium methylate; In methanol; for 3h; Ambient temperature;

DOI:10.1016/0008-6215(84)85168-X

upstream raw materials:

methanesulfonyl chloride

2,3,4,2',3',4'-hexa-(benzyloxy)-6-acetyloxy-α,α-trehalose

[(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl]-methanol

Downstream raw materials:

2,3,4,2',3',4'-hexa-O-benzyl-6'-O-(methylsulfonyl)-α-α-trehalose

2,3,4,2',3',4'-hexa-O-benzyl-6-O-corynomycoloyl-α-α-trehalose

6-O-corynomycoloyl-α,α-trehalose