p-tolyl 2-O-benzoyl-4-O-benzyl-3-O-(naphthalen-2-ylmethyl)-1-thio-β-D-glucopyranoside

Base Information

Chemical Name:p-tolyl 2-O-benzoyl-4-O-benzyl-3-O-(naphthalen-2-ylmethyl)-1-thio-β-D-glucopyranoside
CAS No.:942044-54-4
Molecular Formula:C₃₈H₃₆O₆S
Molecular Weight:620.766
Hs Code.:

Synonyms:p-tolyl 2-O-benzoyl-4-O-benzyl-3-O-(naphthalen-2-ylmethyl)-1-thio-β-D-glucopyranoside

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Chemical Property of p-tolyl 2-O-benzoyl-4-O-benzyl-3-O-(naphthalen-2-ylmethyl)-1-thio-β-D-glucopyranoside

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Technology Process of p-tolyl 2-O-benzoyl-4-O-benzyl-3-O-(naphthalen-2-ylmethyl)-1-thio-β-D-glucopyranoside

There total 4 articles about p-tolyl 2-O-benzoyl-4-O-benzyl-3-O-(naphthalen-2-ylmethyl)-1-thio-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: 92.0%

: 942044-20-4
p-tolyl 2-O-benzoyl-4,6-O-benzylidene-3-O-(naphthalene-2-ylmethyl)-1-thio-β-D-glucopyranoside

: 942044-54-4
p-tolyl 2-O-benzoyl-4-O-benzyl-3-O-(naphthalen-2-ylmethyl)-1-thio-β-D-glucopyranoside

Guidance literature:: p-tolyl 2-O-benzoyl-4,6-O-benzylidene-3-O-(naphthalene-2-ylmethyl)-1-thio-β-D-glucopyranoside; In tetrahydrofuran; at 20 ℃; for 1h; Molecular sieve;

With borane-THF; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; at -40 - 20 ℃; for 25h; Molecular sieve;
DOI:10.1002/ejoc.201500229

Reference yield:

: 942043-54-1
p-methylphenyl 4,6-O-benzylidine-3-O-(naphthalen-2-ylmethyl)-1-thio-β-D-glucopyranoside

: 942044-54-4
p-tolyl 2-O-benzoyl-4-O-benzyl-3-O-(naphthalen-2-ylmethyl)-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: pyridine; dmap / dichloromethane / 20 °C

2: borane-THF; copper(II) bis(trifluoromethanesulfonate) / dichloromethane / 0 °C

With pyridine; dmap; borane-THF; copper(II) bis(trifluoromethanesulfonate); In dichloromethane;
DOI:10.1021/jo201586r

Reference yield:

: 939-26-4
2-bromomethylnaphthyl bromide

: 942044-54-4
p-tolyl 2-O-benzoyl-4-O-benzyl-3-O-(naphthalen-2-ylmethyl)-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: di(n-butyl)tin oxide / toluene / 3 h / Reflux

1.2: 20 °C

2.1: pyridine; dmap / dichloromethane / 20 °C

3.1: borane-THF; copper(II) bis(trifluoromethanesulfonate) / dichloromethane / 0 °C

With pyridine; dmap; borane-THF; copper(II) bis(trifluoromethanesulfonate); di(n-butyl)tin oxide; In dichloromethane; toluene;
DOI:10.1021/jo201586r