p-tolyl 4-O-acetyl-2,3-O-isopropylidene-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-acetyl-1-thio-α-L-rhamnopyranoside

Base Information

Chemical Name:p-tolyl 4-O-acetyl-2,3-O-isopropylidene-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-acetyl-1-thio-α-L-rhamnopyranoside
CAS No.:943221-75-8
Molecular Formula:C₂₈H₃₈O₁₁S
Molecular Weight:582.669
Hs Code.:

Synonyms:p-tolyl 4-O-acetyl-2,3-O-isopropylidene-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-acetyl-1-thio-α-L-rhamnopyranoside

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Chemical Property of p-tolyl 4-O-acetyl-2,3-O-isopropylidene-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-acetyl-1-thio-α-L-rhamnopyranoside

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Technology Process of p-tolyl 4-O-acetyl-2,3-O-isopropylidene-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-acetyl-1-thio-α-L-rhamnopyranoside

There total 3 articles about p-tolyl 4-O-acetyl-2,3-O-isopropylidene-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-acetyl-1-thio-α-L-rhamnopyranoside 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: 99.9%

: 943221-79-2
p-tolyl 2,4-di-O-acetyl-1-thio-α-L-rhamnopyranoside

: 83866-17-5
4-O-acetyl-2,3-O-isopropylidene-1-O-trichloroacetimidoyl-α-L-rhamnopyranose

: 943221-75-8
p-tolyl 4-O-acetyl-2,3-O-isopropylidene-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-acetyl-1-thio-α-L-rhamnopyranoside

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; 4 Angstroem MS; In dichloromethane; at -20 ℃; for 0.5h;
DOI:10.1016/j.carres.2007.03.014

Reference yield:

: 851625-43-9
p-tolyl 4-O-acetyl-2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

: 943221-75-8
p-tolyl 4-O-acetyl-2,3-O-isopropylidene-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-acetyl-1-thio-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: N-bromosuccinimide / acetone; H₂O / 0.08 h / -20 °C

1.2: 237.1 mg / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 4 h / 0 °C

2.1: 99.9 percent / 4 Angstroem MS; TMSOTf / CH₂Cl₂ / 0.5 h / -20 °C

With N-Bromosuccinimide; trimethylsilyl trifluoromethanesulfonate; 4 Angstroem MS; In dichloromethane; water; acetone;
DOI:10.1016/j.carres.2007.03.014

Reference yield:

: 628308-75-8
(2S,3S,4R,5R,6S)-2-methyl-6-(p-tolylthio)tetrahydro-2H-pyranol

: 943221-75-8
p-tolyl 4-O-acetyl-2,3-O-isopropylidene-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-acetyl-1-thio-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: triethylorthoacetate; (1S)-(+)-champhor-10-sulfonic acid / dimethylformamide / 4 h

1.2: 4-N,N-dimethylaminopyridine; Et₃N / 1 h / 20 °C

1.3: 71.5 percent / HCl; water

2.1: 99.9 percent / 4 Angstroem MS; TMSOTf / CH₂Cl₂ / 0.5 h / -20 °C

With trimethylsilyl trifluoromethanesulfonate; 4 Angstroem MS; Triethyl orthoacetate; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.carres.2007.03.014