O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl) trichloroacetimidate

Base Information

• Chemical Name: O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl) trichloroacetimidate
• CAS No.: 303752-87-6
• Molecular Formula: C₂₉H₂₈Cl₃NO₆
• Molecular Weight: 592.903
• Mol file: 303752-87-6.mol

Synonyms:O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl) trichloroacetimidate

Chemical Property of O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl) trichloroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl) trichloroacetimidate

There total 6 articles about O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl) trichloroacetimidate 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: 77.0%

2,3-Bis-O-(phenylmethyl)-4,6-O-(phenylmethylene)-D-galactopyranose (168037-64-7) + trichloroacetonitrile (545-06-2) → O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl) trichloroacetimidate (303752-87-6)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 0.666667h;

DOI:10.1016/S0008-6215(00)00092-6

Reference yield:

2,3-Bis-O-(phenylmethyl)-4,6-O-(phenylmethylene)-D-galactopyranose (168037-64-7) + trichloroacetonitrile (545-06-2) → O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranosyl) trichloroacetimidate + O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl) trichloroacetimidate (303752-87-6)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 2h; optical yield given as %de; Inert atmosphere;

DOI:10.1021/ol1001895

Reference yield:

benzyl bromide (100-39-0) → O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl) trichloroacetimidate (303752-87-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 69 percent / NaH / dimethylformamide / 1 h / 0 - 20 °C

2: 74 percent / NaOAc / PdCl₂ / acetic acid; H₂O

3: 77 percent / DBU / CH₂Cl₂ / 0.67 h / 20 °C

With sodium acetate; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium dichloride; In dichloromethane; water; acetic acid; N,N-dimethyl-formamide; 1: Alkylation / 2: ether cleavage / 3: Substitution;

DOI:10.1016/S0008-6215(00)00092-6

upstream raw materials:

2,3-Bis-O-(phenylmethyl)-4,6-O-(phenylmethylene)-D-galactopyranose

trichloroacetonitrile

benzyl bromide

4,6-O-benzylidene-α,β-D-galactopyranose

Downstream raw materials:

(2S,3S,4R)-2-azido-1-(((2S,4aS,6S,7R,8S,8aR)-7,8-bis(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy)octadecane-3,4-diol

1-O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)-2-O-methanesulfonyl-D-arabino-1,2,3,4-octadecantetrol

(2S,3R,4R)-2-tert-butyldimethylsilyloxy-3,4-O-isopropylideneoctadecyl-2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside

(2S,3R,4R)-2-tert-butyldimethylsilyloxy-3,4-O-isopropylideneoctadecyl-2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranoside