allyl 4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Base Information

• Chemical Name: allyl 4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside
• CAS No.: 183388-21-8
• Molecular Formula: C₁₉H₂₂Cl₃NO₇
• Molecular Weight: 482.745
• Mol file: 183388-21-8.mol

Synonyms:allyl 4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Chemical Property of allyl 4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl 4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

There total 7 articles about allyl 4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside 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: 76.0%

benzaldehyde dimethyl acetal (1125-88-8) + 2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose (172490-46-9) + allyl alcohol (107-18-6) → allyl 4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside (183388-21-8)

Guidance literature:

2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose; allyl alcohol; With chloro-trimethyl-silane; at 20 ℃; for 72h;

benzaldehyde dimethyl acetal; With toluene-4-sulfonic acid; In acetonitrile; at 20 ℃;

DOI:10.1271/bbb.66.211

Reference yield: 76.0%

allyl 4,6‐O‐benzylidene‐2‐deoxy‐3‐methoxycarbonyl‐2‐(2,2,2‐trichloroethoxycarbonylamino)‐α‐D‐glucopyranoside (1202384-99-3) → allyl 4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside (183388-21-8)

Guidance literature:

With pyridine; acetic acid; lithium iodide; for 4h; chemoselective reaction; Reflux;

DOI:10.1016/j.tetlet.2009.09.174

Reference yield:

2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose (172490-46-9) → allyl 4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside (183388-21-8)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen chloride / 0.33 h / Heating

2: 12.3 g / (+)-camphor-10-sulfonic acid / tetrahydrofuran / 3 h / Heating

With hydrogenchloride; (+)-10-camphorsulfonic acid; In tetrahydrofuran; 1: Etherification / 2: Cyclization;

DOI:10.1246/bcsj.70.1435

upstream raw materials:

allyl-2-N-Troc-2-deoxy-α-D-glucopyranoside

benzaldehyde

benzaldehyde dimethyl acetal

2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose

Downstream raw materials:

allyl 4,6-O-benzylidene-3-O-[(R)-3-(benzyloxy)tetradecanoyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

allyl 4,6-O-benzylidene-2-deoxy-3-O-[(S)-3-(tetradecanoyloxy)tetradecanoyl]-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

allyl (R)-4,6-O-benzylidene-2-deoxy-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

(R)-3-Dodecyloxy-tetradecanoic acid (2R,4aR,6S,7R,8R,8aS)-6-allyloxy-2-phenyl-7-(2,2,2-trichloro-ethoxycarbonylamino)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester