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

Base Information

• Chemical Name: 1,6-anhydro-2,3,2',3'-tetra-O-benzyl-4',6'-O-benzylidene-β-maltose
• CAS No.: 85395-84-2
• Molecular Formula: C₄₇H₄₈O₁₀
• Molecular Weight: 772.892
• Mol file: 85395-84-2.mol

Synonyms:1,6-anhydro-2,3,2',3'-tetra-O-benzyl-4',6'-O-benzylidene-β-maltose

Chemical Property of 1,6-anhydro-2,3,2',3'-tetra-O-benzyl-4',6'-O-benzylidene-β-maltose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,6-anhydro-2,3,2',3'-tetra-O-benzyl-4',6'-O-benzylidene-β-maltose

There total 1 articles about 1,6-anhydro-2,3,2',3'-tetra-O-benzyl-4',6'-O-benzylidene-β-maltose 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:

2,3,2',3'-tetra-O-acetyl-1,6-anhydro-4',6'-O-benzylidene-β-maltose (56838-37-0) + benzyl bromide (100-39-0) → 1,6-anhydro-2,3,2',3'-tetra-O-benzyl-4',6'-O-benzylidene-β-maltose (85395-84-2)

Guidance literature:

With sodium methylate; sodium hydride; Yield given. Multistep reaction; 1.) methanol, r.t., overnight; 2.) DMF, r.t., 30 min; 3.) r.t., 3 h;

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

Reference yield: 63.0%

1,6-anhydro-2,3,2',3'-tetra-O-benzyl-4',6'-O-benzylidene-β-maltose (85395-84-2) → 1,6-anhydro-2,3,2',3'-tetra-O-benzyl-β-maltose (85395-85-3)

Guidance literature:

With water; acetic acid; at 97 - 98 ℃; for 0.5h;

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

Reference yield:

1,6-anhydro-2,3,2',3'-tetra-O-benzyl-4',6'-O-benzylidene-β-maltose (85395-84-2) → 4'-amino-1,6-anhydro-2,2',3,3'-tetra-O-benzyl-4',6'-dideoxy-β-maltose (85395-93-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 63 percent / water, acetic acid / 0.5 h / 97 - 98 °C

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

3: 80 percent / lithium aluminium hydride / various solvent(s) / 2 h / Ambient temperature

4: 93 percent / pyridine; CH₂Cl₂ / 48 h / Ambient temperature

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

6: 94 percent / 1.) triethylamine, 4-(dimethylamino)pyridine; 2.) water / CH₂Cl₂ / 1.) 0 deg C, 3 h; 2.) r.t., 2 h

7: 83 percent / sodium azide / hexamethylphosphoric acid triamide / 10 h / 90 - 100 °C

8: 84 percent / lithium aluminium hydride / diethyl ether / 10 h / Heating

With sodium benzoate; dmap; sodium hydroxide; N-iodo-succinimide; lithium aluminium tetrahydride; sodium azide; water; acetic acid; triethylamine; triphenylphosphine; In pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane;

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

upstream raw materials:

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

benzyl bromide

Downstream raw materials:

1,6-anhydro-2,2',3,3',6'-penta-O-benzyl-β-maltose

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

Acetic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-((1R,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-tetrahydro-pyran-3-yl ester

Acetic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-((2R,3R,4S,5R)-4,5-bis-benzyloxy-6-methylsulfanyl-2-phenylcarbamoyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester