Benzoic acid (2R,3R,4R,5R,6R)-3-azido-6-benzyloxymethyl-2-(2,2,2-trichloro-acetimidoyloxy)-5-(2,2,2-trifluoro-ethoxysulfonyloxy)-tetrahydro-pyran-4-yl ester

Base Information

Chemical Name:Benzoic acid (2R,3R,4R,5R,6R)-3-azido-6-benzyloxymethyl-2-(2,2,2-trichloro-acetimidoyloxy)-5-(2,2,2-trifluoro-ethoxysulfonyloxy)-tetrahydro-pyran-4-yl ester
CAS No.:640273-65-0
Molecular Formula:C₂₄H₂₂Cl₃F₃N₄O₉S
Molecular Weight:705.88
Hs Code.:

Benzoic acid (2R,3R,4R,5R,6R)-3-azido-6-benzyloxymethyl-2-(2,2,2-trichloro-acetimidoyloxy)-5-(2,2,2-trifluoro-ethoxysulfonyloxy)-tetrahydro-pyran-4-yl ester

Synonyms:Benzoic acid (2R,3R,4R,5R,6R)-3-azido-6-benzyloxymethyl-2-(2,2,2-trichloro-acetimidoyloxy)-5-(2,2,2-trifluoro-ethoxysulfonyloxy)-tetrahydro-pyran-4-yl ester

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Chemical Property of Benzoic acid (2R,3R,4R,5R,6R)-3-azido-6-benzyloxymethyl-2-(2,2,2-trichloro-acetimidoyloxy)-5-(2,2,2-trifluoro-ethoxysulfonyloxy)-tetrahydro-pyran-4-yl ester

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Technology Process of Benzoic acid (2R,3R,4R,5R,6R)-3-azido-6-benzyloxymethyl-2-(2,2,2-trichloro-acetimidoyloxy)-5-(2,2,2-trifluoro-ethoxysulfonyloxy)-tetrahydro-pyran-4-yl ester

There total 7 articles about Benzoic acid (2R,3R,4R,5R,6R)-3-azido-6-benzyloxymethyl-2-(2,2,2-trichloro-acetimidoyloxy)-5-(2,2,2-trifluoro-ethoxysulfonyloxy)-tetrahydro-pyran-4-yl ester 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:

: 545-06-2
trichloroacetonitrile

: Benzoic acid (3R,4R,5R,6R)-3-azido-6-benzyloxymethyl-2-hydroxy-5-(2,2,2-trifluoro-ethoxysulfonyloxy)-tetrahydro-pyran-4-yl ester

: Benzoic acid (2S,3R,4R,5R,6R)-3-azido-6-benzyloxymethyl-2-(2,2,2-trichloro-acetimidoyloxy)-5-(2,2,2-trifluoro-ethoxysulfonyloxy)-tetrahydro-pyran-4-yl ester

: 640273-65-0
Benzoic acid (2R,3R,4R,5R,6R)-3-azido-6-benzyloxymethyl-2-(2,2,2-trichloro-acetimidoyloxy)-5-(2,2,2-trifluoro-ethoxysulfonyloxy)-tetrahydro-pyran-4-yl ester

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃;
DOI:10.1021/ol035882w

Reference yield:

: 98-88-4
benzoyl chloride

: 640273-65-0
Benzoic acid (2R,3R,4R,5R,6R)-3-azido-6-benzyloxymethyl-2-(2,2,2-trichloro-acetimidoyloxy)-5-(2,2,2-trifluoro-ethoxysulfonyloxy)-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 94 percent / pyridine

2: 57 percent / Et₃SiH; trifluoromethanesulfonic acid; 4 Angstroem molecular sieves / CH₂Cl₂ / -78 °C

3: sulfur trioxide-trimethylamine complex / dimethylformamide / 50 °C

4: citric acid / acetonitrile / 20 °C

5: tetrabutylammonium fluoride; acetic acid / tetrahydrofuran / -25 °C

6: DBU / CH₂Cl₂ / 0 °C

With pyridine; triethylsilane; trifluorormethanesulfonic acid; 4 A molecular sieve; tetrabutyl ammonium fluoride; sulfur trioxide trimethylamine complex; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; citric acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ol035882w

Reference yield:

: 212246-68-9
thexyldimethylsilyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside

: 640273-65-0
Benzoic acid (2R,3R,4R,5R,6R)-3-azido-6-benzyloxymethyl-2-(2,2,2-trichloro-acetimidoyloxy)-5-(2,2,2-trifluoro-ethoxysulfonyloxy)-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 94 percent / pyridine

2: 57 percent / Et₃SiH; trifluoromethanesulfonic acid; 4 Angstroem molecular sieves / CH₂Cl₂ / -78 °C

3: sulfur trioxide-trimethylamine complex / dimethylformamide / 50 °C

4: citric acid / acetonitrile / 20 °C

5: tetrabutylammonium fluoride; acetic acid / tetrahydrofuran / -25 °C

6: DBU / CH₂Cl₂ / 0 °C

With pyridine; triethylsilane; trifluorormethanesulfonic acid; 4 A molecular sieve; tetrabutyl ammonium fluoride; sulfur trioxide trimethylamine complex; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; citric acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ol035882w