1,6-anhydro-2,3-di-O-benzyl-4-O-<2,3-di-O-benzyl-6-deoxy-4-O-(methylsulfonyl)-α-D-galactopyranosyl>-β-D-glucopyranose

Base Information

• Chemical Name: 1,6-anhydro-2,3-di-O-benzyl-4-O-<2,3-di-O-benzyl-6-deoxy-4-O-(methylsulfonyl)-α-D-galactopyranosyl>-β-D-glucopyranose
• CAS No.: 85395-91-1
• Molecular Formula: C₄₁H₄₆O₁₁S
• Molecular Weight: 746.876
• Mol file: 85395-91-1.mol

Synonyms:1,6-anhydro-2,3-di-O-benzyl-4-O-<2,3-di-O-benzyl-6-deoxy-4-O-(methylsulfonyl)-α-D-galactopyranosyl>-β-D-glucopyranose

Chemical Property of 1,6-anhydro-2,3-di-O-benzyl-4-O-<2,3-di-O-benzyl-6-deoxy-4-O-(methylsulfonyl)-α-D-galactopyranosyl>-β-D-glucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,6-anhydro-2,3-di-O-benzyl-4-O-<2,3-di-O-benzyl-6-deoxy-4-O-(methylsulfonyl)-α-D-galactopyranosyl>-β-D-glucopyranose

There total 9 articles about 1,6-anhydro-2,3-di-O-benzyl-4-O-<2,3-di-O-benzyl-6-deoxy-4-O-(methylsulfonyl)-α-D-galactopyranosyl>-β-D-glucopyranose 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: 94.0%

methanesulfonyl chloride (124-63-0) + 1,6-anhydro-2,3-di-O-benzyl-4-O-(2,3-di-O-benzyl-6-deoxy-α-D-galactopyranosyl)-β-D-glucopyranose (85395-90-0) → 1,6-anhydro-2,3-di-O-benzyl-4-O-<2,3-di-O-benzyl-6-deoxy-4-O-(methylsulfonyl)-α-D-galactopyranosyl>-β-D-glucopyranose (85395-91-1)

Guidance literature:

With dmap; water; triethylamine; In dichloromethane; 1.) 0 deg C, 3 h; 2.) r.t., 2 h;

DOI:10.1016/0008-6215(83)88173-7

Reference yield:

benzyl bromide (100-39-0) → 1,6-anhydro-2,3-di-O-benzyl-4-O-<2,3-di-O-benzyl-6-deoxy-4-O-(methylsulfonyl)-α-D-galactopyranosyl>-β-D-glucopyranose (85395-91-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) 0.42 M methanolic sodium methoxide; 2.) sodium hydride / 1.) methanol, r.t., overnight; 2.) DMF, r.t., 30 min; 3.) r.t., 3 h

2: 63 percent / water, acetic acid / 0.5 h / 97 - 98 °C

3: 74 percent / 1.) triphenylphosphine, N-iodosuccinimide / 1.) DMF, 50 deg C, 3 h; 2.) DMF, methanol, r.t., 1 h

4: 80 percent / lithium aluminium hydride / various solvent(s) / 2 h / Ambient temperature

5: 93 percent / pyridine; CH₂Cl₂ / 48 h / Ambient temperature

6: 1.) sodium benzoate; 2.) 2 M aqueous sodium hydroxide / 1.) hexamethylphosphoric triamide, 120-130 deg C, 16 h; 2.) methanol, r.t., overnight

7: 94 percent / 1.) triethylamine, 4-(dimethylamino)pyridine; 2.) water / CH₂Cl₂ / 1.) 0 deg C, 3 h; 2.) r.t., 2 h

With sodium benzoate; dmap; sodium hydroxide; N-iodo-succinimide; lithium aluminium tetrahydride; water; sodium methylate; sodium hydride; acetic acid; triethylamine; triphenylphosphine; In pyridine; dichloromethane;

DOI:10.1016/0008-6215(83)88173-7

Reference yield:

2,3,2',3'-tetra-O-acetyl-1,6-anhydro-4',6'-O-benzylidene-β-maltose (56838-37-0) → 1,6-anhydro-2,3-di-O-benzyl-4-O-<2,3-di-O-benzyl-6-deoxy-4-O-(methylsulfonyl)-α-D-galactopyranosyl>-β-D-glucopyranose (85395-91-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) 0.42 M methanolic sodium methoxide; 2.) sodium hydride / 1.) methanol, r.t., overnight; 2.) DMF, r.t., 30 min; 3.) r.t., 3 h

2: 63 percent / water, acetic acid / 0.5 h / 97 - 98 °C

3: 74 percent / 1.) triphenylphosphine, N-iodosuccinimide / 1.) DMF, 50 deg C, 3 h; 2.) DMF, methanol, r.t., 1 h

4: 80 percent / lithium aluminium hydride / various solvent(s) / 2 h / Ambient temperature

5: 93 percent / pyridine; CH₂Cl₂ / 48 h / Ambient temperature

6: 1.) sodium benzoate; 2.) 2 M aqueous sodium hydroxide / 1.) hexamethylphosphoric triamide, 120-130 deg C, 16 h; 2.) methanol, r.t., overnight

7: 94 percent / 1.) triethylamine, 4-(dimethylamino)pyridine; 2.) water / CH₂Cl₂ / 1.) 0 deg C, 3 h; 2.) r.t., 2 h

With sodium benzoate; dmap; sodium hydroxide; N-iodo-succinimide; lithium aluminium tetrahydride; water; sodium methylate; sodium hydride; acetic acid; triethylamine; triphenylphosphine; In pyridine; dichloromethane;

DOI:10.1016/0008-6215(83)88173-7

upstream raw materials:

methanesulfonyl chloride

1,6-anhydro-2,3-di-O-benzyl-4-O-(2,3-di-O-benzyl-6-deoxy-α-D-galactopyranosyl)-β-D-glucopyranose

2,3,2',3'-tetra-O-acetyl-1,6-anhydro-4',6'-O-benzylidene-β-maltose

benzyl bromide

Downstream raw materials:

1,6-anhydro-4'-azido-2,3,2',3'-tetra-O-benzyl-4',6'-dideoxy-β-maltose

4'-amino-1,6-anhydro-2,2',3,3'-tetra-O-benzyl-4',6'-dideoxy-β-maltose