3,4,6-tri-O-benzyl-2-fluoro-2-deoxy-α-D-galactopyranosyl trichloroacetimidate

Base Information

• Chemical Name: 3,4,6-tri-O-benzyl-2-fluoro-2-deoxy-α-D-galactopyranosyl trichloroacetimidate
• CAS No.: 1240035-65-7
• Molecular Formula: C₂₉H₂₉Cl₃FNO₅
• Molecular Weight: 596.91

Synonyms:3,4,6-tri-O-benzyl-2-fluoro-2-deoxy-α-D-galactopyranosyl trichloroacetimidate

Chemical Property of 3,4,6-tri-O-benzyl-2-fluoro-2-deoxy-α-D-galactopyranosyl trichloroacetimidate

Chemical Property:

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Technology Process of 3,4,6-tri-O-benzyl-2-fluoro-2-deoxy-α-D-galactopyranosyl trichloroacetimidate

There total 1 articles about 3,4,6-tri-O-benzyl-2-fluoro-2-deoxy-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: 92.0%

2-deoxy-2-fluoro-3,4,6-tri-O-benzyl-α,β-D-galactopyranose + trichloroacetonitrile (545-06-2) → 3,4,6-tri-O-benzyl-2-fluoro-2-deoxy-α-D-galactopyranosyl trichloroacetimidate (1240035-65-7)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 - 20 ℃; for 0.75h;

DOI:10.1002/ejoc.201501081

Reference yield: 89.0%

3,4,6-tri-O-benzyl-2-fluoro-2-deoxy-α-D-galactopyranosyl trichloroacetimidate (1240035-65-7) + benzyl alcohol (100-51-6,185532-71-2) → 1-O-benzyl-3,4,6-tri-O-benzyl-2-deoxy-2-fluoro-β-D-galactopyranose (1393354-68-1)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 ℃; for 2h; stereoselective reaction; Inert atmosphere;

DOI:10.1002/chem.201200468

Reference yield: 85.0%

3,4,6-tri-O-benzyl-2-fluoro-2-deoxy-α-D-galactopyranosyl trichloroacetimidate (1240035-65-7) + isopropyl alcohol (67-63-0,8013-70-5) → 1-O-isopropyl-3,4,6-tri-O-benzyl-2-deoxy-2-fluoro-β-D-galactopyranose (1393354-05-6)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 ℃; for 2h; stereoselective reaction; Inert atmosphere;

DOI:10.1002/chem.201200468

upstream raw materials:

trichloroacetonitrile

Downstream raw materials:

Fmoc-Thr(β-2F-Bn3Gal-(1->3)-α-4,6-O-Bzn-GalNAc)-OtBu

N-(9H-fluoren-9-yl)-methoxycarbonyl-O-(2-acetamido-2,6-dideoxy-6-fluoro-3-O-[3,4,6-tri-O-benzyl-2-deoxy-2-fluoro-β-D-galactopyranosyl]-α-D-galactopyranosyl)-L-threonine tert-butyl ester

N-(9H-fluoren-9-yl)-methoxycarbonyl-O-(2-acetamido-2,6-dideoxy-6,6-difluoro-3-O-[3,4,6-tri-O-benzyl-2-deoxy-2-fluoro-β-D-galactopyranosyl]-α-D-galactopyranosyl)-L-threonine tert-butyl ester

2-deoxy-2-fluoro-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->1)-(2S,3R,E)-2-amino-3-O-benzyl-4-octadecene-1,3-diol

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