diosgenyl 4-O-(tri-O-acetyl-α-L-arabinofuranosyl)-2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-6-O-benzoyl-3-O-pivaloyl-β-D-glucopyranoside

Base Information

Chemical Name:diosgenyl 4-O-(tri-O-acetyl-α-L-arabinofuranosyl)-2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-6-O-benzoyl-3-O-pivaloyl-β-D-glucopyranoside
CAS No.:222719-12-2
Molecular Formula:C₆₈H₉₄O₂₄
Molecular Weight:1295.48
Hs Code.:

Synonyms:diosgenyl 4-O-(tri-O-acetyl-α-L-arabinofuranosyl)-2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-6-O-benzoyl-3-O-pivaloyl-β-D-glucopyranoside

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Chemical Property of diosgenyl 4-O-(tri-O-acetyl-α-L-arabinofuranosyl)-2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-6-O-benzoyl-3-O-pivaloyl-β-D-glucopyranoside

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Technology Process of diosgenyl 4-O-(tri-O-acetyl-α-L-arabinofuranosyl)-2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-6-O-benzoyl-3-O-pivaloyl-β-D-glucopyranoside

There total 14 articles about diosgenyl 4-O-(tri-O-acetyl-α-L-arabinofuranosyl)-2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-6-O-benzoyl-3-O-pivaloyl-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: 93.0%

: 2,3,5-tri-O-acetyl-α,β-L-arabinofuranosyl trichloroacetimidate

: 213753-23-2
diosgenyl 2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-6-O-benzoyl-3-O-pivaloyl-β-D-glucopyranoside

: 222719-12-2
diosgenyl 4-O-(tri-O-acetyl-α-L-arabinofuranosyl)-2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-6-O-benzoyl-3-O-pivaloyl-β-D-glucopyranoside

Guidance literature:: With 4 Angstroem MS; boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1016/S0040-4039(98)01354-9

Reference yield: 93.0%

: 213753-23-2
diosgenyl 2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-6-O-benzoyl-3-O-pivaloyl-β-D-glucopyranoside

: 335591-65-6
2,3,5-tri-O-acetyl-α-L-arabinofuranosyl trichloroacetimidate

: 222719-12-2
diosgenyl 4-O-(tri-O-acetyl-α-L-arabinofuranosyl)-2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-6-O-benzoyl-3-O-pivaloyl-β-D-glucopyranoside

Guidance literature:: With 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1016/S0008-6215(99)00066-X

Reference yield:

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

: 222719-12-2
diosgenyl 4-O-(tri-O-acetyl-α-L-arabinofuranosyl)-2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-6-O-benzoyl-3-O-pivaloyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 50 percent / 4A molecular sieves; NIS; AgOTf / CH₂Cl₂; toluene / 1 h / -30 °C

2: 85 percent / NaOMe / methanol; CH₂Cl₂ / 50 °C / pH 15

3: 64 percent / pyridine / 2 h / 20 °C

4: 100 percent / 4A molecular sieves; BF₃*OEt₂ / CH₂Cl₂ / 1 h / -40 °C

5: 80 percent / TsOH*H₂O / methanol; CH₂Cl₂ / 2 h / 20 °C

6: 75 percent / pyridine / CH₂Cl₂ / -20 °C

7: 93 percent / 4A molecular sieves; BF₃*OEt₂ / CH₂Cl₂ / 0.5 h / 0 °C

With pyridine; N-iodo-succinimide; 4 A molecular sieve; boron trifluoride diethyl etherate; sodium methylate; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; In methanol; dichloromethane; toluene; 1: Etherification / 2: deprotection / 3: Acetylation / 4: Etherification / 5: deprotection / 6: Acetylation / 7: Etherification;
DOI:10.1016/S0008-6215(99)00066-X