diosgenyl 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 Name:diosgenyl 2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-6-O-benzoyl-3-O-pivaloyl-β-D-glucopyranoside
CAS No.:213753-23-2
Molecular Formula:C₅₇H₈₀O₁₇
Molecular Weight:1037.25
Hs Code.:

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

There total 10 articles about diosgenyl 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: 75.0%

: 98-88-4
benzoyl chloride

: 222719-08-6
diosgenyl 2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-3-O-pivaloyl-β-D-glucopyranoside

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

Guidance literature:: With pyridine; at 0 ℃; for 2h;
DOI:10.1016/S0040-4039(98)01354-9

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

: 213753-23-2
diosgenyl 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 6 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

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;
DOI:10.1016/S0008-6215(99)00066-X

Reference yield:

: 213753-21-0
diosgenyl 4,6-O-benzylidene-3-O-pivaloyl-β-D-glucopyranoside

: 213753-23-2
diosgenyl 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 3 steps

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

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

3: 75 percent / pyridine / CH₂Cl₂ / -20 °C

With pyridine; 4 A molecular sieve; boron trifluoride diethyl etherate; toluene-4-sulfonic acid; In methanol; dichloromethane; 1: Etherification / 2: deprotection / 3: Acetylation;
DOI:10.1016/S0008-6215(99)00066-X