(3R,3aR,4R,5R,7R,7aR)-4,5-Dihydroxy-3-((R)-1-hydroxy-ethyl)-7-phenylselanylmethyl-2-p-tolylmethanesulfonyl-octahydro-isoindol-1-one

Base Information

Chemical Name:(3R,3aR,4R,5R,7R,7aR)-4,5-Dihydroxy-3-((R)-1-hydroxy-ethyl)-7-phenylselanylmethyl-2-p-tolylmethanesulfonyl-octahydro-isoindol-1-one
CAS No.:88549-89-7
Molecular Formula:C₂₅H₃₁NO₆SSe
Molecular Weight:552.55
Hs Code.:

Synonyms:(3R,3aR,4R,5R,7R,7aR)-4,5-Dihydroxy-3-((R)-1-hydroxy-ethyl)-7-phenylselanylmethyl-2-p-tolylmethanesulfonyl-octahydro-isoindol-1-one

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Chemical Property of (3R,3aR,4R,5R,7R,7aR)-4,5-Dihydroxy-3-((R)-1-hydroxy-ethyl)-7-phenylselanylmethyl-2-p-tolylmethanesulfonyl-octahydro-isoindol-1-one

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Technology Process of (3R,3aR,4R,5R,7R,7aR)-4,5-Dihydroxy-3-((R)-1-hydroxy-ethyl)-7-phenylselanylmethyl-2-p-tolylmethanesulfonyl-octahydro-isoindol-1-one

There total 20 articles about (3R,3aR,4R,5R,7R,7aR)-4,5-Dihydroxy-3-((R)-1-hydroxy-ethyl)-7-phenylselanylmethyl-2-p-tolylmethanesulfonyl-octahydro-isoindol-1-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: 90.0%

: 51419-59-1
4-methylbenzylsulfonyl chloride

: 88549-88-6
(3aR,5R,5aR,8R,8aR,8bR)-2,2-Dimethyl-5-phenylselanylmethyl-8-[(R)-1-(tetrahydro-pyran-2-yloxy)-ethyl]-octahydro-[1,3]dioxolo[4,5-e]isoindol-6-one

: 88549-89-7
(3R,3aR,4R,5R,7R,7aR)-4,5-Dihydroxy-3-((R)-1-hydroxy-ethyl)-7-phenylselanylmethyl-2-p-tolylmethanesulfonyl-octahydro-isoindol-1-one

Guidance literature:: With n-butyllithium; toluene-4-sulfonic acid; 2.) MeOH;
DOI:10.1021/ja00316a062

Reference yield:

: (1R,3aR,4R,6R,7R,7aR)-6,7-Dihydroxy-1-((R)-1-hydroxy-ethyl)-3-oxo-octahydro-isoindole-4-carboxylic acid methyl ester

: 88549-89-7
(3R,3aR,4R,5R,7R,7aR)-4,5-Dihydroxy-3-((R)-1-hydroxy-ethyl)-7-phenylselanylmethyl-2-p-tolylmethanesulfonyl-octahydro-isoindol-1-one

Guidance literature:: Multi-step reaction with 7 steps

1: p-toluenesulfonic acid / tetrahydrofuran

2: p-toluenesulfonic acid / CH₂Cl₂

3: LiAlH₄ / tetrahydrofuran

4: Et₃N / CH₂Cl₂

5: 96 percent / NaBH₄ / ethanol

6: n-BuLi / -78 °C

7: p-toluenesulfonic acid / methanol

With sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane;

Reference yield:

: 88549-83-1
(1R,3aR,4R,7aR)-3-Oxo-1-[(R)-1-(tetrahydro-pyran-2-yloxy)-ethyl]-2,3,3a,4,5,7a-hexahydro-1H-isoindole-4-carboxylic acid

: 88549-89-7
(3R,3aR,4R,5R,7R,7aR)-4,5-Dihydroxy-3-((R)-1-hydroxy-ethyl)-7-phenylselanylmethyl-2-p-tolylmethanesulfonyl-octahydro-isoindol-1-one

Guidance literature:: Multi-step reaction with 13 steps

1: 100 percent / I₂, NaHCO₃ / H₂O; CH₂Cl₂

2: aq. NaOH / tetrahydrofuran

3: methanol

4: p-toluenesulfonic acid / methanol

5: H₂O / 2 h / 50 - 60 °C

6: Et₃N / methanol

7: p-toluenesulfonic acid / tetrahydrofuran

8: p-toluenesulfonic acid / CH₂Cl₂

9: LiAlH₄ / tetrahydrofuran

10: Et₃N / CH₂Cl₂

11: 96 percent / NaBH₄ / ethanol

12: n-BuLi / -78 °C

13: p-toluenesulfonic acid / methanol

With sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; iodine; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane; water;