phenyl 6-O-benzyloxymethyl-2-deoxy-1-thio-3-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

Base Information

Chemical Name:phenyl 6-O-benzyloxymethyl-2-deoxy-1-thio-3-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside
CAS No.:188583-28-0
Molecular Formula:C₂₆H₂₇Cl₆NO₉S
Molecular Weight:742.286
Hs Code.:

Synonyms:phenyl 6-O-benzyloxymethyl-2-deoxy-1-thio-3-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

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Chemical Property of phenyl 6-O-benzyloxymethyl-2-deoxy-1-thio-3-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

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Technology Process of phenyl 6-O-benzyloxymethyl-2-deoxy-1-thio-3-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

There total 7 articles about phenyl 6-O-benzyloxymethyl-2-deoxy-1-thio-3-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-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: 71.0%

: 3587-60-8
Benzyloxymethyl chloride

: 188583-27-9
phenyl 2-deoxy-1-thio-3-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

: 188583-28-0
phenyl 6-O-benzyloxymethyl-2-deoxy-1-thio-3-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

Guidance literature:: With tetramethylurea; In dichloromethane; for 24h; Ambient temperature;
DOI:10.1248/cpb.45.312

Reference yield:

: 108-98-5
thiophenol

: 188583-28-0
phenyl 6-O-benzyloxymethyl-2-deoxy-1-thio-3-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 89 percent / BF₃*Et₂O / CH₂Cl₂ / 24 h / Ambient temperature

2: 88 percent / NaOMe / methanol / 0.33 h / 0 °C

3: 87 percent / p-TsOH / dimethylformamide / 2 h / Ambient temperature

4: 93 percent / 4-dimethylaminopyridine, pyridine / CH₂Cl₂ / 10 h / Ambient temperature

5: 91 percent / 83percent aq. AcOH / 2 h / Ambient temperature

6: 71 percent / 1,1,3,3-tetramethylurea / CH₂Cl₂ / 24 h / Ambient temperature

With pyridine; dmap; boron trifluoride diethyl etherate; sodium methylate; toluene-4-sulfonic acid; acetic acid; tetramethylurea; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1248/cpb.45.312

Reference yield:

: 122210-01-9,122210-05-3,145416-95-1,146864-65-5,114360-77-9
1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose

: 188583-28-0
phenyl 6-O-benzyloxymethyl-2-deoxy-1-thio-3-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 89 percent / BF₃*Et₂O / CH₂Cl₂ / 24 h / Ambient temperature

2: 88 percent / NaOMe / methanol / 0.33 h / 0 °C

3: 87 percent / p-TsOH / dimethylformamide / 2 h / Ambient temperature

4: 93 percent / 4-dimethylaminopyridine, pyridine / CH₂Cl₂ / 10 h / Ambient temperature

5: 91 percent / 83percent aq. AcOH / 2 h / Ambient temperature

6: 71 percent / 1,1,3,3-tetramethylurea / CH₂Cl₂ / 24 h / Ambient temperature

With pyridine; dmap; boron trifluoride diethyl etherate; sodium methylate; toluene-4-sulfonic acid; acetic acid; tetramethylurea; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1248/cpb.45.312