2,3,2',3'-tetra-O-benzyl-4,6;4',6'-di-O-benzylidene-α,α-D-trehalose

Base Information

• Chemical Name: 2,3,2',3'-tetra-O-benzyl-4,6;4',6'-di-O-benzylidene-α,α-D-trehalose
• CAS No.: 149113-51-9
• Molecular Formula: C₅₄H₅₄O₁₁
• Molecular Weight: 879.016
• Mol file: 149113-51-9.mol

Synonyms:2,3,2',3'-tetra-O-benzyl-4,6;4',6'-di-O-benzylidene-α,α-D-trehalose

Chemical Property of 2,3,2',3'-tetra-O-benzyl-4,6;4',6'-di-O-benzylidene-α,α-D-trehalose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,2',3'-tetra-O-benzyl-4,6;4',6'-di-O-benzylidene-α,α-D-trehalose

There total 3 articles about 2,3,2',3'-tetra-O-benzyl-4,6;4',6'-di-O-benzylidene-α,α-D-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: 69.0%

benzyl bromide (100-39-0) + 4,6;4',6'-di-O-benzylidene-α,α-D-trehalose (18929-82-3,60949-45-3,97390-02-8,127128-52-3) → 2,3,2',3'-tetra-O-benzyl-4,6;4',6'-di-O-benzylidene-α,α-D-trehalose (149113-51-9)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; for 18h; Inert atmosphere;

DOI:10.1080/14756366.2020.1837125

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → 2,3,2',3'-tetra-O-benzyl-4,6;4',6'-di-O-benzylidene-α,α-D-trehalose (149113-51-9)

Guidance literature:

Multi-step reaction with 2 steps

1: H⁽¹⁺⁾ / dimethylformamide / 4 h / 80 °C

2: KH

With hydrogen cation; potassium hydride; In N,N-dimethyl-formamide;

DOI:10.1021/ol9908979

Reference yield:

TREHALOSE (99-20-7) + benzaldehyde dimethyl acetal (1125-88-8) → 2,3,2',3'-tetra-O-benzyl-4,6;4',6'-di-O-benzylidene-α,α-D-trehalose (149113-51-9)

Guidance literature:

Multi-step reaction with 2 steps

1: camphor-10-sulfonic acid / N,N-dimethyl-formamide / 60 °C / 105.01 Torr / Inert atmosphere

2: sodium hydride; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide; mineral oil / 18 h / 0 °C / Inert atmosphere

With camphor-10-sulfonic acid; tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; mineral oil;

DOI:10.1039/c3ob41389f

upstream raw materials:

benzyl bromide

4,6;4',6'-di-O-benzylidene-α,α-D-trehalose

benzaldehyde dimethyl acetal

TREHALOSE

Downstream raw materials:

[(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

2,3,4,2',3'-penta-O-benzyl-4',6'-O-benzylidene-α,α-D-trehalose

2,3,6-tri-O-benzyl-α-D-glucopyranosyl 2,3,6-tri-O-benzylidene-α-D-glucopyranoside

2',3'-di-O-benzyl-α-D-glucopyranosyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside