(5S,6R,7R,8S)-5-[4-chloro-3-(4-pyrrolidin-1-yl-benzyl)-phenyl]-4-oxa-spiro[2.5]octane-6,7,8-triol

Base Information

Chemical Name:(5S,6R,7R,8S)-5-[4-chloro-3-(4-pyrrolidin-1-yl-benzyl)-phenyl]-4-oxa-spiro[2.5]octane-6,7,8-triol
CAS No.:1290630-20-4
Molecular Formula:C₂₄H₂₈ClNO₄
Molecular Weight:429.944
Hs Code.:

Synonyms:(5S,6R,7R,8S)-5-[4-chloro-3-(4-pyrrolidin-1-yl-benzyl)-phenyl]-4-oxa-spiro[2.5]octane-6,7,8-triol

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Chemical Property of (5S,6R,7R,8S)-5-[4-chloro-3-(4-pyrrolidin-1-yl-benzyl)-phenyl]-4-oxa-spiro[2.5]octane-6,7,8-triol

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Technology Process of (5S,6R,7R,8S)-5-[4-chloro-3-(4-pyrrolidin-1-yl-benzyl)-phenyl]-4-oxa-spiro[2.5]octane-6,7,8-triol

There total 16 articles about (5S,6R,7R,8S)-5-[4-chloro-3-(4-pyrrolidin-1-yl-benzyl)-phenyl]-4-oxa-spiro[2.5]octane-6,7,8-triol 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:

: 1290630-19-1
(5S,6S,7R,8S)-5-(4-chloro-3-(4-(pyrrolidin-1-yl)benzyl)phenyl)-4-oxaspiro[2.5]octane-6,7,8-triyl triacetate

: 1290630-20-4
(5S,6R,7R,8S)-5-[4-chloro-3-(4-pyrrolidin-1-yl-benzyl)-phenyl]-4-oxa-spiro[2.5]octane-6,7,8-triol

Guidance literature:: With sodium methylate; In methanol; at 20 ℃; for 3h;

Reference yield:

: 461432-26-8,1373321-04-0
dapagliflozin

: 1290630-20-4
(5S,6R,7R,8S)-5-[4-chloro-3-(4-pyrrolidin-1-yl-benzyl)-phenyl]-4-oxa-spiro[2.5]octane-6,7,8-triol

Guidance literature:: Multi-step reaction with 10 steps

1.1: 1H-imidazole; triphenylphosphine; iodine / dichloromethane / 18 h / 0 °C / Reflux

2.1: sodium methylate / methanol / 0 - 45 °C

3.1: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C

3.2: 18 h / 20 °C

4.1: diethylzinc / hexane; diethyl ether / 8 h / 20 - 40 °C

5.1: hydrogenchloride; hydrogen; water / palladium 10% on activated carbon / methanol / 18 h / 20 °C

6.1: dmap; pyridine / dichloromethane / 20 °C

7.1: boron tribromide / dichloromethane / -78 - -15 °C

8.1: pyridine / 0 - 20 °C

9.1: sodium t-butanolate; johnphos / palladium diacetate / toluene / 0.25 h / Inert atmosphere

9.2: 0.25 h / Inert atmosphere

10.1: sodium methylate / methanol / 3 h / 20 °C

With pyridine; 1H-imidazole; hydrogenchloride; dmap; water; hydrogen; iodine; diethylzinc; sodium methylate; boron tribromide; sodium hydride; triphenylphosphine; johnphos; sodium t-butanolate; palladium 10% on activated carbon; palladium diacetate; In methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;

Reference yield:

: 1219000-72-2
(2S,3R,4R,5S,6S)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(iodomethyl)tetrahydro-2H-pyran-3,4,5-triol

: 1290630-20-4
(5S,6R,7R,8S)-5-[4-chloro-3-(4-pyrrolidin-1-yl-benzyl)-phenyl]-4-oxa-spiro[2.5]octane-6,7,8-triol

Guidance literature:: Multi-step reaction with 9 steps

1.1: sodium methylate / methanol / 0 - 45 °C

2.1: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C

2.2: 18 h / 20 °C

3.1: diethylzinc / hexane; diethyl ether / 8 h / 20 - 40 °C

4.1: hydrogenchloride; hydrogen; water / palladium 10% on activated carbon / methanol / 18 h / 20 °C

5.1: dmap; pyridine / dichloromethane / 20 °C

6.1: boron tribromide / dichloromethane / -78 - -15 °C

7.1: pyridine / 0 - 20 °C

8.1: sodium t-butanolate; johnphos / palladium diacetate / toluene / 0.25 h / Inert atmosphere

8.2: 0.25 h / Inert atmosphere

9.1: sodium methylate / methanol / 3 h / 20 °C

With pyridine; hydrogenchloride; dmap; water; hydrogen; diethylzinc; sodium methylate; boron tribromide; sodium hydride; johnphos; sodium t-butanolate; palladium 10% on activated carbon; palladium diacetate; In methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;