diosgenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranoside

Base Information

Chemical Name:diosgenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranoside
CAS No.:213753-20-9
Molecular Formula:C₅₄H₆₄O₁₀
Molecular Weight:873.096
Hs Code.:

Synonyms:diosgenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranoside

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of diosgenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranoside

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Technology Process of diosgenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranoside

There total 7 articles about diosgenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-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: 50.0%

: 149563-08-6
(2R,4aR,6S,7R,8S,8aR)-6-(ethylthio)-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diyl dibenzoate

: 512-04-9
diosgenin

: 213753-20-9
diosgenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranoside

Guidance literature:: With N-iodo-succinimide; 4 Angstroem MS; silver trifluoromethanesulfonate; In dichloromethane; at -20 ℃; for 0.5h;
DOI:10.1016/S0040-4039(98)01354-9

Reference yield:

: 63783-77-7
2,3,4,6-tetra-O-acetyl-glucosylthioacetate

: 213753-20-9
diosgenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: Cleland's reagent; sodium hydrogencarbonate / N,N-dimethyl acetamide / 2 h / 20 °C

2: triethylamine / acetonitrile / 0.5 h / 20 °C

3: potassium carbonate / methanol / 1 h / 20 °C

4: camphorsulfonic acid / acetonitrile / 12 h / 20 °C / Inert atmosphere

5: triethylamine; dmap / dichloromethane / 3 h / 0 - 20 °C

6: bis-[(trifluoroacetoxy)iodo]benzene / acetonitrile; water / 0.17 h / 20 °C

7: trifluoromethylsulfonic anhydride; 2,6-di-tert-butyl-4-methylpyridine; 1,2-dimethoxy-4-(2-propenyl)benzene / dichloromethane / 0.5 h / 0 °C / Molecular sieve

With dmap; 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; 1,2-dimethoxy-4-(2-propenyl)benzene; sodium hydrogencarbonate; potassium carbonate; triethylamine; bis-[(trifluoroacetoxy)iodo]benzene; Cleland's reagent; In methanol; dichloromethane; N,N-dimethyl acetamide; water; acetonitrile;
DOI:10.1021/jacs.6b08305

Reference yield:

: S-2-(2-propylthio)benzyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside

: 213753-20-9
diosgenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: potassium carbonate / methanol / 1 h / 20 °C

2: camphorsulfonic acid / acetonitrile / 12 h / 20 °C / Inert atmosphere

3: triethylamine; dmap / dichloromethane / 3 h / 0 - 20 °C

4: bis-[(trifluoroacetoxy)iodo]benzene / acetonitrile; water / 0.17 h / 20 °C

5: trifluoromethylsulfonic anhydride; 2,6-di-tert-butyl-4-methylpyridine; 1,2-dimethoxy-4-(2-propenyl)benzene / dichloromethane / 0.5 h / 0 °C / Molecular sieve

With dmap; 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; 1,2-dimethoxy-4-(2-propenyl)benzene; potassium carbonate; triethylamine; bis-[(trifluoroacetoxy)iodo]benzene; In methanol; dichloromethane; water; acetonitrile;
DOI:10.1021/jacs.6b08305