phenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→4)-2,3-di-O-acetyl-6-O-benzoyl-1-thio-β-D-glucopyranoside

Base Information

Chemical Name:phenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→4)-2,3-di-O-acetyl-6-O-benzoyl-1-thio-β-D-glucopyranoside
CAS No.:257614-56-5
Molecular Formula:C₃₅H₄₀O₁₅S
Molecular Weight:732.76
Hs Code.:

Synonyms:phenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→4)-2,3-di-O-acetyl-6-O-benzoyl-1-thio-β-D-glucopyranoside

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Chemical Property of phenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→4)-2,3-di-O-acetyl-6-O-benzoyl-1-thio-β-D-glucopyranoside

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Technology Process of phenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→4)-2,3-di-O-acetyl-6-O-benzoyl-1-thio-β-D-glucopyranoside

There total 7 articles about phenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→4)-2,3-di-O-acetyl-6-O-benzoyl-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: 87.0%

: 113893-72-4
2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate

: 257614-51-0
phenyl 2,3-di-O-acetyl-6-O-benzoyl-1-thio-β-D-glucopyranoside

: 257614-56-5
phenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→4)-2,3-di-O-acetyl-6-O-benzoyl-1-thio-β-D-glucopyranoside

Guidance literature:: 2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate; phenyl 2,3-di-O-acetyl-6-O-benzoyl-1-thio-β-D-glucopyranoside; In dichloromethane; at 0 ℃; for 0.333333h; Molecular sieve;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 0.5h; Molecular sieve;
DOI:10.1016/j.ejmech.2017.11.040

Reference yield:

: 71676-30-7,87508-18-7,138922-03-9,87508-17-6
(2R,4aR,6S,7R,8R,8aS)-2-Phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

: 257614-56-5
phenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→4)-2,3-di-O-acetyl-6-O-benzoyl-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: pyridine

2: 80 percent HOAc / 50 °C

3: 93 percent / pyridine / -10 °C

4: trimethylsilyl trifluoromethanesulfonate,; 4 A MS / CH₂Cl₂ / -70 - 20 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; acetic acid; In dichloromethane; 1: Acetylation / 2: Hydrolysis / 3: Acylation / 4: glycosylation;
DOI:10.1021/ja9926818

Reference yield:

: 152983-23-8
phenyl 2,3-di-O-acetyl-4,6-di-O-benzylidene-1-thio-β-D-glucopyranoside

: 257614-56-5
phenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→4)-2,3-di-O-acetyl-6-O-benzoyl-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 80 percent HOAc / 50 °C

2: 93 percent / pyridine / -10 °C

3: trimethylsilyl trifluoromethanesulfonate,; 4 A MS / CH₂Cl₂ / -70 - 20 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; acetic acid; In dichloromethane; 1: Hydrolysis / 2: Acylation / 3: glycosylation;
DOI:10.1021/ja9926818