phenyl 3-O-benzyl-4,6-O-benzylidene-5-C-(2-tosyloxymethyl)-1-thio-β-D-glucopyranoside

Base Information

Chemical Name:phenyl 3-O-benzyl-4,6-O-benzylidene-5-C-(2-tosyloxymethyl)-1-thio-β-D-glucopyranoside
CAS No.:753502-51-1
Molecular Formula:C₃₄H₃₄O₈S₂
Molecular Weight:634.771
Hs Code.:

Synonyms:phenyl 3-O-benzyl-4,6-O-benzylidene-5-C-(2-tosyloxymethyl)-1-thio-β-D-glucopyranoside

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Chemical Property of phenyl 3-O-benzyl-4,6-O-benzylidene-5-C-(2-tosyloxymethyl)-1-thio-β-D-glucopyranoside

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Technology Process of phenyl 3-O-benzyl-4,6-O-benzylidene-5-C-(2-tosyloxymethyl)-1-thio-β-D-glucopyranoside

There total 10 articles about phenyl 3-O-benzyl-4,6-O-benzylidene-5-C-(2-tosyloxymethyl)-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:

: 98-59-9
p-toluenesulfonyl chloride

: 612841-76-6
phenyl 3-O-benzyl-4,6-O-benzylidene-5-C-hydroxymethyl-1-thio-β-D-glucopyranoside

: 753502-51-1
phenyl 3-O-benzyl-4,6-O-benzylidene-5-C-(2-tosyloxymethyl)-1-thio-β-D-glucopyranoside

Guidance literature:: With dmap; In pyridine; at 20 ℃; for 15h;
DOI:10.1016/S0040-4039(03)01631-9

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 753502-51-1
phenyl 3-O-benzyl-4,6-O-benzylidene-5-C-(2-tosyloxymethyl)-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: 8.28 g / camphorsulphonic acid / dimethylformamide / 14 h / 20 °C

2.1: O₃ / CH₂Cl₂ / 0.03 h / -78 °C

2.2: Me₂S / CH₂Cl₂ / 1 h / -78 - 20 °C

3.1: 858 mg / NaBH₄ / ethanol / 18 h / 20 °C

4.1: pyridine; DMAP / 22 h / 20 °C

With pyridine; dmap; sodium tetrahydroborate; camphor-10-sulfonic acid; ozone; In ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2004.06.009

Reference yield:

: (2R,3S,4S,5R,6S)-4-Benzyloxy-2-hydroxymethyl-6-phenylsulfanyl-2-vinyl-tetrahydro-pyran-3,5-diol

: 753502-51-1
phenyl 3-O-benzyl-4,6-O-benzylidene-5-C-(2-tosyloxymethyl)-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: 8.28 g / camphorsulphonic acid / dimethylformamide / 14 h / 20 °C

2.1: O₃ / CH₂Cl₂ / 0.03 h / -78 °C

2.2: Me₂S / CH₂Cl₂ / 1 h / -78 - 20 °C

3.1: 858 mg / NaBH₄ / ethanol / 18 h / 20 °C

4.1: pyridine; DMAP / 22 h / 20 °C

With pyridine; dmap; sodium tetrahydroborate; camphor-10-sulfonic acid; ozone; In ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2004.06.009