di-O-benzyl 4,6-O-diacetyl-3-O-((R)-phenylsulfonylethylpropion-2-yl)-N-acetyl-α-D-glucosamine-1-phosphate

Base Information

Chemical Name:di-O-benzyl 4,6-O-diacetyl-3-O-((R)-phenylsulfonylethylpropion-2-yl)-N-acetyl-α-D-glucosamine-1-phosphate
CAS No.:202464-67-3
Molecular Formula:C₃₇H₄₄NO₁₅PS
Molecular Weight:805.794
Hs Code.:

Synonyms:di-O-benzyl 4,6-O-diacetyl-3-O-((R)-phenylsulfonylethylpropion-2-yl)-N-acetyl-α-D-glucosamine-1-phosphate

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Chemical Property of di-O-benzyl 4,6-O-diacetyl-3-O-((R)-phenylsulfonylethylpropion-2-yl)-N-acetyl-α-D-glucosamine-1-phosphate

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Technology Process of di-O-benzyl 4,6-O-diacetyl-3-O-((R)-phenylsulfonylethylpropion-2-yl)-N-acetyl-α-D-glucosamine-1-phosphate

There total 12 articles about di-O-benzyl 4,6-O-diacetyl-3-O-((R)-phenylsulfonylethylpropion-2-yl)-N-acetyl-α-D-glucosamine-1-phosphate 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: 61.0%

: 67746-43-4
dibenzyl N,N-diethylphosphoramidite

: 4,6-O-diacetyl-3-O-((R)-phenylsulfonylethyl-propion-2-yl)-N-acetyl-D-glucosamine

: 202464-67-3
di-O-benzyl 4,6-O-diacetyl-3-O-((R)-phenylsulfonylethylpropion-2-yl)-N-acetyl-α-D-glucosamine-1-phosphate

Guidance literature:: dibenzyl N,N-diethylphosphoramidite; 4,6-O-diacetyl-3-O-((R)-phenylsulfonylethyl-propion-2-yl)-N-acetyl-D-glucosamine; With 1H-tetrazole; In dichloromethane; acetonitrile; at 20 ℃; for 17.5h; Inert atmosphere;

With tert.-butylhydroperoxide; In tetrahydrofuran; decane; at -10 - 20 ℃; for 20h; Inert atmosphere;
DOI:10.1002/chem.201604279

Reference yield: 32.0%

: (R)-2-[(2R,3S,4R,5R,6R)-3-Acetoxy-2-acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphanyloxy)-tetrahydro-pyran-4-yloxy]-propionic acid 2-benzenesulfonyl-ethyl ester

: 202464-67-3
di-O-benzyl 4,6-O-diacetyl-3-O-((R)-phenylsulfonylethylpropion-2-yl)-N-acetyl-α-D-glucosamine-1-phosphate

Guidance literature:: With dihydrogen peroxide; In tetrahydrofuran; at -70 - 20 ℃;
DOI:10.1016/S0960-894X(01)00653-9

Reference yield:

: 20611-21-6
2-(phenylsulfonyl)ethanol

: 202464-67-3
di-O-benzyl 4,6-O-diacetyl-3-O-((R)-phenylsulfonylethylpropion-2-yl)-N-acetyl-α-D-glucosamine-1-phosphate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 96 percent / DMAP; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 2 h / 0 - 20 °C

2.1: AcOH; H₂O / 45 h / Heating

2.2: pyridine / 0 - 20 °C

2.3: H₂; AcOH / Pd/C / 16 h

3.1: 1,2,4-triazole / CH₂Cl₂ / 20 °C

4.1: 32 percent / 30 percent H₂O₂ / tetrahydrofuran / -70 - 20 °C

With 1,2,4-Triazole; dmap; water; dihydrogen peroxide; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0960-894X(01)00653-9