2,3,4-O-tribenzyl-α-L-rhamnosyl(1->3)-4-O-acetyl-2-O-benzoyl-1-O-trichloroacetimido-α-L-rhamnopyranoside

Base Information

Chemical Name:2,3,4-O-tribenzyl-α-L-rhamnosyl(1->3)-4-O-acetyl-2-O-benzoyl-1-O-trichloroacetimido-α-L-rhamnopyranoside
CAS No.:944153-63-3
Molecular Formula:C₄₄H₄₆Cl₃NO₁₁
Molecular Weight:871.208
Hs Code.:

Synonyms:2,3,4-O-tribenzyl-α-L-rhamnosyl(1->3)-4-O-acetyl-2-O-benzoyl-1-O-trichloroacetimido-α-L-rhamnopyranoside

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Chemical Property of 2,3,4-O-tribenzyl-α-L-rhamnosyl(1->3)-4-O-acetyl-2-O-benzoyl-1-O-trichloroacetimido-α-L-rhamnopyranoside

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Technology Process of 2,3,4-O-tribenzyl-α-L-rhamnosyl(1->3)-4-O-acetyl-2-O-benzoyl-1-O-trichloroacetimido-α-L-rhamnopyranoside

There total 14 articles about 2,3,4-O-tribenzyl-α-L-rhamnosyl(1->3)-4-O-acetyl-2-O-benzoyl-1-O-trichloroacetimido-α-L-rhamnopyranoside 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: 83.0%

: 2,3,4-O-tribenzyl-α-L-rhamnosyl(1->3)-4-O-acetyl-2-O-benzoyl-α,β-L-rhamnopyranoside

: 545-06-2
trichloroacetonitrile

: 944153-63-3
2,3,4-O-tribenzyl-α-L-rhamnosyl(1->3)-4-O-acetyl-2-O-benzoyl-1-O-trichloroacetimido-α-L-rhamnopyranoside

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1055/s-2007-965995

Reference yield:

: 944153-56-4
2,3-O-(4-methoxy)benzylidene-1-(4-tolyl)thio-α,β-L-rhamnopyranoside

: 944153-63-3
2,3,4-O-tribenzyl-α-L-rhamnosyl(1->3)-4-O-acetyl-2-O-benzoyl-1-O-trichloroacetimido-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: DMAP / pyridine / 0.5 h / 20 °C

2.1: sodium cyanoborohydride; 4 Angstroem molecular sieves; TFA / tetrahydrofuran / 16 h / 20 °C

2.2: DMAP / pyridine / 0.5 h / 20 °C

2.3: 64 mg / cerium(IV) ammonium nitrate; H₂O / acetonitrile / 2 h / 20 °C

3.1: 78 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / 0 - 20 °C

4.1: 92 percent / NBS; H₂O / acetone / 2 h / 20 °C

5.1: 83 percent / DBU / CH₂Cl₂ / 1 h / 20 °C

With dmap; N-Bromosuccinimide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; water; sodium cyanoborohydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; In tetrahydrofuran; pyridine; dichloromethane; acetone;
DOI:10.1055/s-2007-965995

Reference yield:

: 944153-54-2
4-O-acetyl-2-O-benzoyl-1-(4-tolyl)thio-α-L-rhamnopyranoside

: 944153-63-3
2,3,4-O-tribenzyl-α-L-rhamnosyl(1->3)-4-O-acetyl-2-O-benzoyl-1-O-trichloroacetimido-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 78 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / 0 - 20 °C

2: 92 percent / NBS; H₂O / acetone / 2 h / 20 °C

3: 83 percent / DBU / CH₂Cl₂ / 1 h / 20 °C

With N-Bromosuccinimide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; water; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; acetone;
DOI:10.1055/s-2007-965995