p-tolyl 3,6-di-O-benzyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxy)carbamoylamino-β-D-glucopyranoside

Base Information

Chemical Name:p-tolyl 3,6-di-O-benzyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxy)carbamoylamino-β-D-glucopyranoside
CAS No.:502692-44-6
Molecular Formula:C₃₀H₃₂Cl₃NO₆S
Molecular Weight:641.012
Hs Code.:

Synonyms:p-tolyl 3,6-di-O-benzyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxy)carbamoylamino-β-D-glucopyranoside

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Chemical Property of p-tolyl 3,6-di-O-benzyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxy)carbamoylamino-β-D-glucopyranoside

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Technology Process of p-tolyl 3,6-di-O-benzyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxy)carbamoylamino-β-D-glucopyranoside

There total 20 articles about p-tolyl 3,6-di-O-benzyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxy)carbamoylamino-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: 90.0%

: 905267-00-7
p-tolyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-2-(2,2,2-trichloroethoxy)carbamoylamino-β-D-glucopyranoside

: 502692-44-6
p-tolyl 3,6-di-O-benzyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxy)carbamoylamino-β-D-glucopyranoside

Guidance literature:: With hydrogenchloride; 3 A molecular sieve; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; at 0 ℃; for 0.5h;
DOI:10.1016/j.carres.2006.01.007

Reference yield: 90.0%

: 502692-43-5
(2R,3S,4R,5R,6S)-5-Amino-4-benzyloxy-2-benzyloxymethyl-6-p-tolylsulfanyl-tetrahydro-pyran-3-ol

: 17341-93-4
2,2,2-Trichloroethyl chloroformate

: 502692-44-6
p-tolyl 3,6-di-O-benzyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxy)carbamoylamino-β-D-glucopyranoside

Guidance literature:: With sodium hydrogencarbonate; In tetrahydrofuran; at 20 ℃; for 4h;
DOI:10.1021/jo0206420

Reference yield:

: 100-52-7
benzaldehyde

: 502692-44-6
p-tolyl 3,6-di-O-benzyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxy)carbamoylamino-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: triethylsilyl trifluoromethyl sulfonate / toluene; tetrahydrofuran / 0.75 h / -20 °C / Inert atmosphere

1.2: 2 h / -20 °C / Inert atmosphere

2.1: sodium cyanoborohydride; hydrogenchloride / diethyl ether; tetrahydrofuran / 16 h / 0 °C / Molecular sieve; Inert atmosphere

With hydrogenchloride; triethylsilyl trifluoromethyl sulfonate; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; toluene;
DOI:10.1021/jacs.9b01991