(1R,2S,7S,7aS)-1-Hydroxy-7-[(4-methoxybenzyl)oxy]-2-{[(4-methylphenyl)sulfonyl]oxy}hexahydro-1H-pyrrolizine

Base Information

Chemical Name:(1R,2S,7S,7aS)-1-Hydroxy-7-[(4-methoxybenzyl)oxy]-2-{[(4-methylphenyl)sulfonyl]oxy}hexahydro-1H-pyrrolizine
CAS No.:369379-08-8
Molecular Formula:C₂₂H₂₇NO₆S
Molecular Weight:433.525
Hs Code.:

Synonyms:(1R,2S,7S,7aS)-1-Hydroxy-7-[(4-methoxybenzyl)oxy]-2-{[(4-methylphenyl)sulfonyl]oxy}hexahydro-1H-pyrrolizine

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Chemical Property of (1R,2S,7S,7aS)-1-Hydroxy-7-[(4-methoxybenzyl)oxy]-2-{[(4-methylphenyl)sulfonyl]oxy}hexahydro-1H-pyrrolizine

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Technology Process of (1R,2S,7S,7aS)-1-Hydroxy-7-[(4-methoxybenzyl)oxy]-2-{[(4-methylphenyl)sulfonyl]oxy}hexahydro-1H-pyrrolizine

There total 12 articles about (1R,2S,7S,7aS)-1-Hydroxy-7-[(4-methoxybenzyl)oxy]-2-{[(4-methylphenyl)sulfonyl]oxy}hexahydro-1H-pyrrolizine 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: 57.0%

: 98-59-9
p-toluenesulfonyl chloride

: (1R,2S,7S,7aS)-1,2-dihydroxy-7-(4-methoxybenzyloxy)hexahydro-1H-pyrrolizine-borane

: 369379-08-8
(1R,2S,7S,7aS)-1-Hydroxy-7-[(4-methoxybenzyl)oxy]-2-{[(4-methylphenyl)sulfonyl]oxy}hexahydro-1H-pyrrolizine

: 369379-10-2
(1R,2S,7S,7aR)-1,2-Bis{[(4-methylphenyl)sulfonyl]oxy}-7-[(4-methoxybenzyl)oxy]hexahydro-1H-pyrrolizine

Guidance literature:: p-toluenesulfonyl chloride; (1R,2S,7S,7aS)-1,2-dihydroxy-7-(4-methoxybenzyloxy)hexahydro-1H-pyrrolizine-borane; With triethylamine; In dichloromethane; at 20 ℃; for 44h;

palladium dihydroxide; In methanol; at 20 ℃; for 30h; Further stages.;

Reference yield:

: (2S,4S)-4-(Buta-1,3-dienyl)-2-(4-methoxyphenyl)-1,3-dioxane

: 369379-08-8
(1R,2S,7S,7aS)-1-Hydroxy-7-[(4-methoxybenzyl)oxy]-2-{[(4-methylphenyl)sulfonyl]oxy}hexahydro-1H-pyrrolizine

Guidance literature:: Multi-step reaction with 12 steps

1.1: DIBAL-H / CH₂Cl₂ / 1.5 h / 0 - 20 °C

1.2: 63 percent / I₂ / benzene / 1 h / 20 °C / UV-irradiation

2.1: 2.44 g / (COCl)2; DMSO; Et₃N / dimethylsulfoxide / 1.92 h / -60 °C

3.1: 2.67 g / aq. NaClO₂; NaH₂PO₄*H₂O; 2-methylbut-2-ene / 2-methyl-propan-2-ol / 0.67 h / 0 - 20 °C

4.1: 2.32 g / pyridine / tetrahydrofuran / 20 h / 20 °C

5.1: 1.51 g / hydroxylamine hydrochloride; Et₃N / CH₂Cl₂ / 3 h / 20 °C

6.1: Bu₄NIO₄ / CHCl₃ / 2 h / 22 °C

7.1: 91 percent / Na(Hg); Na₂HPO₄ / ethanol / 14 h / 0 °C

8.1: Et₃N / CH₂Cl₂ / 0.83 h / 0 - 20 °C

9.1: 326 mg / LDA / tetrahydrofuran / 2 h / -78 - 20 °C

10.1: 65 percent / aq. OsO₄; NMO / acetone / 30 h / 20 °C

11.1: 100 percent / BH₃*SMe₂ / tetrahydrofuran / 4 h / 20 °C

12.1: Et₃N / CH₂Cl₂ / 44 h / 20 °C

12.2: 57 percent / Pd(OH)2/C / methanol / 30 h / 20 °C

With pyridine; sodium chlorite; disodium hydrogenphosphate; sodium dihydrogenphosphate; osmium(VIII) oxide; N-methyl-2-indolinone; sodium amalgam; 2-methyl-but-2-ene; oxalyl dichloride; dimethylsulfide borane complex; hydroxylamine hydrochloride; diisobutylaluminium hydride; tetrabutylammonium periodite; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; ethanol; dichloromethane; chloroform; dimethyl sulfoxide; acetone; tert-butyl alcohol; 2.1: Swern oxidation;

Reference yield:

: 290835-94-8
(1S,7aS)-1-(4-Methoxybenzyloxy)-1,2,5,7a-tetrahydro-3H-pyrrolizin-3-one

: 369379-08-8
(1R,2S,7S,7aS)-1-Hydroxy-7-[(4-methoxybenzyl)oxy]-2-{[(4-methylphenyl)sulfonyl]oxy}hexahydro-1H-pyrrolizine

Guidance literature:: Multi-step reaction with 3 steps

1.1: 65 percent / aq. OsO₄; NMO / acetone / 30 h / 20 °C

2.1: 100 percent / BH₃*SMe₂ / tetrahydrofuran / 4 h / 20 °C

3.1: Et₃N / CH₂Cl₂ / 44 h / 20 °C

3.2: 57 percent / Pd(OH)2/C / methanol / 30 h / 20 °C

With osmium(VIII) oxide; N-methyl-2-indolinone; dimethylsulfide borane complex; triethylamine; In tetrahydrofuran; dichloromethane; acetone;