phenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside

Base Information

Chemical Name:phenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside
CAS No.:1394170-32-1
Molecular Formula:C₃₁H₃₆O₁₂S
Molecular Weight:632.686
Hs Code.:

Synonyms:phenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside

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Chemical Property of phenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside

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Technology Process of phenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside

There total 3 articles about phenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-4,6-O-benzylidene-1-deoxy-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: 80.0%

: 1394170-31-0
phenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-3-O-(tert-butyldimethysilyl)-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside

: 1394170-32-1
phenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; Inert atmosphere;
DOI:10.1080/10286020.2011.653348

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 1394170-32-1
phenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 60 °C / pH 2 - 3 / Inert atmosphere

2: 1H-imidazole / dichloromethane / Inert atmosphere; Heating

3: boron trifluoride diethyl etherate / dichloromethane / 3 h / -78 - 20 °C / Molecular sieve; Inert atmosphere

4: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere

With 1H-imidazole; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1080/10286020.2011.653348

Reference yield:

: 2936-70-1,5624-48-6,13992-15-9,16758-34-2,28244-97-5,77481-62-0,77481-63-1,105088-17-3,149495-84-1
(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol

: 1394170-32-1
phenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 60 °C / pH 2 - 3 / Inert atmosphere

2: 1H-imidazole / dichloromethane / Inert atmosphere; Heating

3: boron trifluoride diethyl etherate / dichloromethane / 3 h / -78 - 20 °C / Molecular sieve; Inert atmosphere

4: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere

With 1H-imidazole; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1080/10286020.2011.653348