4,6:4',6'-di-O-benzylidene-3,3'-di-O-(tetrahydropyran-2-yl)-2,2'-di-O-(trifluoromethylsulfonyl)-α,α-trehalose

Base Information

• Chemical Name: 4,6:4',6'-di-O-benzylidene-3,3'-di-O-(tetrahydropyran-2-yl)-2,2'-di-O-(trifluoromethylsulfonyl)-α,α-trehalose
• CAS No.: 73264-82-1
• Molecular Formula: C₃₈H₄₄F₆O₁₇S₂
• Molecular Weight: 950.88

Synonyms:4,6:4',6'-di-O-benzylidene-3,3'-di-O-(tetrahydropyran-2-yl)-2,2'-di-O-(trifluoromethylsulfonyl)-α,α-trehalose

Chemical Property of 4,6:4',6'-di-O-benzylidene-3,3'-di-O-(tetrahydropyran-2-yl)-2,2'-di-O-(trifluoromethylsulfonyl)-α,α-trehalose

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Technology Process of 4,6:4',6'-di-O-benzylidene-3,3'-di-O-(tetrahydropyran-2-yl)-2,2'-di-O-(trifluoromethylsulfonyl)-α,α-trehalose

There total 2 articles about 4,6:4',6'-di-O-benzylidene-3,3'-di-O-(tetrahydropyran-2-yl)-2,2'-di-O-(trifluoromethylsulfonyl)-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: 88.0%

3,4-dihydro-2H-pyran (110-87-2) + 4,6:4',6'-di-O-benzylidene-2,2'-di-O-(trifluoromethylsulfonyl)-α,α-trehalose (89387-65-5) → 4,6:4',6'-di-O-benzylidene-3,3'-di-O-(tetrahydropyran-2-yl)-2,2'-di-O-(trifluoromethylsulfonyl)-α,α-trehalose (73264-82-1)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; Ambient temperature;

DOI:10.1016/0008-6215(83)88493-6

Reference yield:

4,6-O-benzylidene-α-D-glucopyranosyl-(1→1)-4',6'-O-benzylidene-α-D-glucopyranoside (18929-82-3) → 4,6:4',6'-di-O-benzylidene-3,3'-di-O-(tetrahydropyran-2-yl)-2,2'-di-O-(trifluoromethylsulfonyl)-α,α-trehalose (73264-82-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 23 percent / pyridine / 1.)30 min, ice-bath, 2.) 2h, room temperature

2: 88 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 2 h / Ambient temperature

With pyridine; pyridinium p-toluenesulfonate; In dichloromethane;

DOI:10.1016/0008-6215(84)85304-5

Reference yield: 61.0%

4,6:4',6'-di-O-benzylidene-3,3'-di-O-(tetrahydropyran-2-yl)-2,2'-di-O-(trifluoromethylsulfonyl)-α,α-trehalose (73264-82-1) → C50H58O13

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium benzoate; at 115 ℃; for 72h;

DOI:10.1016/0008-6215(83)88493-6

upstream raw materials:

3,4-dihydro-2H-pyran

4,6:4',6'-di-O-benzylidene-2,2'-di-O-(trifluoromethylsulfonyl)-α,α-trehalose

4,6-O-benzylidene-α-D-glucopyranosyl-(1→1)-4',6'-O-benzylidene-α-D-glucopyranoside

Downstream raw materials:

2,2'-di-O-benzoyl-4,6:4',6'-di-O-benzylidene-3,3'-di-O-(tetrahydropyran-2-yl)-(α-D-mannopyranosyl α-D-mannopyranoside)

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