(25R)-2α-allyloxycarbonyloxy-3β-(4'-O-benzoyl-2',3'-didehydro-2',3'-dideoxy-α-L-rhamnopyranosyloxy)-5α-spirostan

Base Information

Chemical Name:(25R)-2α-allyloxycarbonyloxy-3β-(4'-O-benzoyl-2',3'-didehydro-2',3'-dideoxy-α-L-rhamnopyranosyloxy)-5α-spirostan
CAS No.:848854-38-6
Molecular Formula:C₄₄H₆₀O₉
Molecular Weight:732.955
Hs Code.:

Synonyms:(25R)-2α-allyloxycarbonyloxy-3β-(4'-O-benzoyl-2',3'-didehydro-2',3'-dideoxy-α-L-rhamnopyranosyloxy)-5α-spirostan

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Chemical Property of (25R)-2α-allyloxycarbonyloxy-3β-(4'-O-benzoyl-2',3'-didehydro-2',3'-dideoxy-α-L-rhamnopyranosyloxy)-5α-spirostan

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Technology Process of (25R)-2α-allyloxycarbonyloxy-3β-(4'-O-benzoyl-2',3'-didehydro-2',3'-dideoxy-α-L-rhamnopyranosyloxy)-5α-spirostan

There total 10 articles about (25R)-2α-allyloxycarbonyloxy-3β-(4'-O-benzoyl-2',3'-didehydro-2',3'-dideoxy-α-L-rhamnopyranosyloxy)-5α-spirostan 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: 74.0%

: 848854-29-5
(25R)-2α-allyloxycarbonyloxy-5α-spirostan-3β-ol

: 34820-21-8
1,5-anhydro-3,4-di-O-benzoyl-2,6-didesoxy-L-arabino-hex-1-enitol

: 848854-38-6
(25R)-2α-allyloxycarbonyloxy-3β-(4'-O-benzoyl-2',3'-didehydro-2',3'-dideoxy-α-L-rhamnopyranosyloxy)-5α-spirostan

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 0.583333h;
DOI:10.1016/j.tetasy.2004.11.028

Reference yield:

: 7404-35-5,17081-04-8,20853-37-6,24332-95-4,27821-10-9,27821-11-0,33947-15-8,34371-40-9,34371-41-0,35521-79-0,36807-81-5,36807-82-6,50615-78-6,51921-33-6,62182-03-0,64913-16-2,70004-81-8,84622-47-9,87303-56-8,108942-32-1,108942-33-2,109430-94-6,143394-72-3,30021-94-4
1,2,3,4-tetra-O-acetyl-L-rhamnopyranose

: 848854-38-6
(25R)-2α-allyloxycarbonyloxy-3β-(4'-O-benzoyl-2',3'-didehydro-2',3'-dideoxy-α-L-rhamnopyranosyloxy)-5α-spirostan

Guidance literature:: Multi-step reaction with 5 steps

1: HBr; Ac₂O / CH₂Cl₂; acetic acid / 2 h / 20 °C

2: 79 percent / zinc; CuSO₄; NaOAc / HOAc; Ac₂O / acetonitrile / 2 h / 20 °C

3: 97 percent / K₂CO₃; MeOH / 24 h / 20 °C

4: 84 percent / pyridine / CH₂Cl₂ / 24 h / 20 °C

5: 74 percent / BF₃*OEt₂ / CH₂Cl₂ / 0.58 h / 0 °C

With pyridine; methanol; boron trifluoride diethyl etherate; hydrogen bromide; sodium acetate; acetic anhydride; potassium carbonate; copper(II) sulfate; zinc; acetic anhydride; In dichloromethane; acetic acid; acetonitrile; 5: Ferrier reaction;
DOI:10.1016/j.tetasy.2004.11.028

Reference yield:

: 69980-52-5
2,3,4-tri-O-acetyl-L-rhamnopyranosyl bromide

: 848854-38-6
(25R)-2α-allyloxycarbonyloxy-3β-(4'-O-benzoyl-2',3'-didehydro-2',3'-dideoxy-α-L-rhamnopyranosyloxy)-5α-spirostan

Guidance literature:: Multi-step reaction with 4 steps

1: 79 percent / zinc; CuSO₄; NaOAc / HOAc; Ac₂O / acetonitrile / 2 h / 20 °C

2: 97 percent / K₂CO₃; MeOH / 24 h / 20 °C

3: 84 percent / pyridine / CH₂Cl₂ / 24 h / 20 °C

4: 74 percent / BF₃*OEt₂ / CH₂Cl₂ / 0.58 h / 0 °C

With pyridine; methanol; boron trifluoride diethyl etherate; sodium acetate; potassium carbonate; copper(II) sulfate; zinc; acetic anhydride; acetic acid; In dichloromethane; acetonitrile; 4: Ferrier reaction;
DOI:10.1016/j.tetasy.2004.11.028