(25R)-3β-(3'-O-benzoyl-2'-bromo-2',6'-dideoxy-α-L-altropyranosyloxy)-5α-spirostan-2-one

Base Information

Chemical Name:(25R)-3β-(3'-O-benzoyl-2'-bromo-2',6'-dideoxy-α-L-altropyranosyloxy)-5α-spirostan-2-one
CAS No.:848854-46-6
Molecular Formula:C₄₀H₅₅BrO₈
Molecular Weight:743.776
Hs Code.:

Synonyms:(25R)-3β-(3'-O-benzoyl-2'-bromo-2',6'-dideoxy-α-L-altropyranosyloxy)-5α-spirostan-2-one

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Chemical Property of (25R)-3β-(3'-O-benzoyl-2'-bromo-2',6'-dideoxy-α-L-altropyranosyloxy)-5α-spirostan-2-one

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Technology Process of (25R)-3β-(3'-O-benzoyl-2'-bromo-2',6'-dideoxy-α-L-altropyranosyloxy)-5α-spirostan-2-one

There total 14 articles about (25R)-3β-(3'-O-benzoyl-2'-bromo-2',6'-dideoxy-α-L-altropyranosyloxy)-5α-spirostan-2-one 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: 42.0%

: 848854-42-2
(25R)-3β-(4'-O-benzoyl-2',3'-didehydro-2',3'-dideoxy-α-L-rhamnopyranosyloxy)-5α-spirostan-2-one

: 848854-46-6
(25R)-3β-(3'-O-benzoyl-2'-bromo-2',6'-dideoxy-α-L-altropyranosyloxy)-5α-spirostan-2-one

: 848854-44-4
(25R)-3β-(4'-O-benzoyl-2'-bromo-2',6'-dideoxy-α-L-altropyranosyloxy)-5α-spirostan-2-one

Guidance literature:: With N-Bromosuccinimide; water; epichlorohydrin; In 1,2-dimethoxyethane; at 0 - 20 ℃; for 2.5h;
DOI:10.1016/j.tetasy.2004.11.028

Reference yield:

: 848854-25-1
(25R)-2α-hydroxy-5α-spirostan-3-one

: 848854-46-6
(25R)-3β-(3'-O-benzoyl-2'-bromo-2',6'-dideoxy-α-L-altropyranosyloxy)-5α-spirostan-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: 7.5 g / pyridine / CH₂Cl₂ / 2 h / -40 - 0 °C

2: 63 percent / sodium borohydride / methanol; tetrahydrofuran / 0.5 h / 20 °C

3: 74 percent / BF₃*OEt₂ / CH₂Cl₂ / 0.58 h / 0 °C

4: 73 percent / tris(dibenzylideneacetone)dipalladium⁽⁰⁾-CHCl₃ adduct; 1,2-bis(diphenylphosphino)ethane / tetrahydrofuran / 6 h / 50 °C

5: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 24 h / 20 °C

6: 29 percent / NBS; H₂O; epichlorohydrin / 1,2-dimethoxy-ethane / 2.5 h / 0 - 20 °C

With pyridine; sodium tetrahydroborate; N-Bromosuccinimide; boron trifluoride diethyl etherate; water; Dess-Martin periodane; epichlorohydrin; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; 1,2-bis-(diphenylphosphino)ethane; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; 3: Ferrier reaction;
DOI:10.1016/j.tetasy.2004.11.028

Reference yield:

: 881175-98-0
(25R)-3-trimethylsilyloxy-5α-spirost-2-ene

: 848854-46-6
(25R)-3β-(3'-O-benzoyl-2'-bromo-2',6'-dideoxy-α-L-altropyranosyloxy)-5α-spirostan-2-one

Guidance literature:: Multi-step reaction with 7 steps

1: dimethyldioxirane / acetone; CH₂Cl₂ / 0.83 h / 0 °C

2: 7.5 g / pyridine / CH₂Cl₂ / 2 h / -40 - 0 °C

3: 63 percent / sodium borohydride / methanol; tetrahydrofuran / 0.5 h / 20 °C

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

5: 73 percent / tris(dibenzylideneacetone)dipalladium⁽⁰⁾-CHCl₃ adduct; 1,2-bis(diphenylphosphino)ethane / tetrahydrofuran / 6 h / 50 °C

6: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 24 h / 20 °C

7: 29 percent / NBS; H₂O; epichlorohydrin / 1,2-dimethoxy-ethane / 2.5 h / 0 - 20 °C

With pyridine; sodium tetrahydroborate; N-Bromosuccinimide; boron trifluoride diethyl etherate; water; 3,3-dimethyldioxirane; Dess-Martin periodane; epichlorohydrin; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; 1,2-bis-(diphenylphosphino)ethane; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; acetone; 4: Ferrier reaction;
DOI:10.1016/j.tetasy.2004.11.028