(3R,3aR,6R,6aS)-benzyl 3-hydroxy-6-(tosyloxy)tetrahydro-2H-furo[3,2-b] pyrrole-4(5H)-carboxylate

Base Information

Chemical Name:(3R,3aR,6R,6aS)-benzyl 3-hydroxy-6-(tosyloxy)tetrahydro-2H-furo[3,2-b] pyrrole-4(5H)-carboxylate
CAS No.:1001547-86-9
Molecular Formula:C₂₁H₂₃NO₇S
Molecular Weight:433.482
Hs Code.:

Synonyms:(3R,3aR,6R,6aS)-benzyl 3-hydroxy-6-(tosyloxy)tetrahydro-2H-furo[3,2-b] pyrrole-4(5H)-carboxylate

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Chemical Property of (3R,3aR,6R,6aS)-benzyl 3-hydroxy-6-(tosyloxy)tetrahydro-2H-furo[3,2-b] pyrrole-4(5H)-carboxylate

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Technology Process of (3R,3aR,6R,6aS)-benzyl 3-hydroxy-6-(tosyloxy)tetrahydro-2H-furo[3,2-b] pyrrole-4(5H)-carboxylate

There total 10 articles about (3R,3aR,6R,6aS)-benzyl 3-hydroxy-6-(tosyloxy)tetrahydro-2H-furo[3,2-b] pyrrole-4(5H)-carboxylate 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: 54.0%

: 1001548-17-9
(3R,3aR,6R,6aS)-3-hydroxyhexahydro-2H-furo[3,2-b]pyrrol-6-yl 4-methylbenzenesulfonate

: 501-53-1,94274-21-2
benzyl chloroformate

: 1001547-86-9
(3R,3aR,6R,6aS)-benzyl 3-hydroxy-6-(tosyloxy)tetrahydro-2H-furo[3,2-b] pyrrole-4(5H)-carboxylate

Guidance literature:: With sodium carbonate; In 1,4-dioxane; water; for 2h;

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 1001547-86-9
(3R,3aR,6R,6aS)-benzyl 3-hydroxy-6-(tosyloxy)tetrahydro-2H-furo[3,2-b] pyrrole-4(5H)-carboxylate

: (1R,4R,5R)-N-(benzyloxycarbonyl)-4-hydroxy-2-oxa-6-azabicyclo<3.3.0>octane

Guidance literature:: (3R,3aR,6R,6aS)-3-hydroxyhexahydro-2H-furo[3,2-b]pyrrol-6-yl 4-methylbenzenesulfonate; With lithium triethylborohydride; In tetrahydrofuran; at 40 ℃; for 1.53333h;

benzyl chloroformate; With sodium carbonate; In tetrahydrofuran; water; at 20 ℃; for 1h; Product distribution / selectivity;

Reference yield:

: 1001548-21-5
(R)-2-amino-1-[(S)-2,5-dihydrofuran-2-yl]ethanol

: 1001547-86-9
(3R,3aR,6R,6aS)-benzyl 3-hydroxy-6-(tosyloxy)tetrahydro-2H-furo[3,2-b] pyrrole-4(5H)-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: sodium carbonate / 1,4-dioxane; water / 1 h / 0 °C

2: pyridine / 19.5 h / 14 - 24 °C

3: Oxone; 1,1,1-trifluoro-2-propanone; sodium hydrogencarbonate; disodium ethylenediamine tetraacetic acid / water; acetonitrile / 5.08 h / 0 °C

4: hydrogen / palladium on activated charcoal / ethanol / 4.5 h

5: sodium carbonate / 1,4-dioxane; water / 2 h

With pyridine; Oxone; 1,1,1-trifluoro-2-propanone; hydrogen; sodium hydrogencarbonate; sodium carbonate; disodium ethylenediamine tetraacetic acid; palladium on activated charcoal; In 1,4-dioxane; ethanol; water; acetonitrile;