(3R,3AS,6AR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-2-hydroxy-1-(4-hydroxybenzyl)propylcarbamate

Base Information

Chemical Name:(3R,3AS,6AR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-2-hydroxy-1-(4-hydroxybenzyl)propylcarbamate
CAS No.:313679-57-1
Molecular Formula:C₂₈H₃₆N₂O₁₀S
Molecular Weight:592.667
Hs Code.:

Synonyms:(3R,3AS,6AR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-2-hydroxy-1-(4-hydroxybenzyl)propylcarbamate

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Chemical Property of (3R,3AS,6AR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-2-hydroxy-1-(4-hydroxybenzyl)propylcarbamate

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Technology Process of (3R,3AS,6AR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-2-hydroxy-1-(4-hydroxybenzyl)propylcarbamate

There total 10 articles about (3R,3AS,6AR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-2-hydroxy-1-(4-hydroxybenzyl)propylcarbamate 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: 98.0%

: 313679-55-9
(3R,3AS,6AR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-1-[4-(benzyloxy)benzyl]-2-hydroxypropylcarbamate

: 313679-57-1
(3R,3AS,6AR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-2-hydroxy-1-(4-hydroxybenzyl)propylcarbamate

Guidance literature:: With hydrogen; palladium on activated charcoal; In tetrahydrofuran;
DOI:10.1016/j.bmcl.2005.05.129 DOI:10.1016/j.bmcl.2006.01.035

Reference yield:

: 162536-84-7
tert-butyl (1S)-2-[4-(benzyloxy)phenyl]-1-[(2S)-oxiranyl]ethylcarbamate

: 313679-57-1
(3R,3AS,6AR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-2-hydroxy-1-(4-hydroxybenzyl)propylcarbamate

Guidance literature:: Multi-step reaction with 5 steps

1: propan-2-ol / Heating

2: DIEA / CH₂Cl₂

3: 100 percent / TFA / CH₂Cl₂

4: 96 percent / DIEA / acetonitrile

5: 98 percent / H₂ / Pd/C / tetrahydrofuran

With hydrogen; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; isopropyl alcohol; acetonitrile;
DOI:10.1016/j.bmcl.2005.05.129

Reference yield:

: 174801-33-3,1059189-63-7
(2S,3S)-N-tert-butoxycarbonyl-3-amino-4-(4-benzyloxyphenyl)-1-chloro-2-hydroxybutane

: 313679-57-1
(3R,3AS,6AR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-2-hydroxy-1-(4-hydroxybenzyl)propylcarbamate

Guidance literature:: Multi-step reaction with 6 steps

1: KOH / ethanol

2: propan-2-ol / Heating

3: DIEA / CH₂Cl₂

4: 100 percent / TFA / CH₂Cl₂

5: 96 percent / DIEA / acetonitrile

6: 98 percent / H₂ / Pd/C / tetrahydrofuran

With potassium hydroxide; hydrogen; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; isopropyl alcohol; acetonitrile;
DOI:10.1016/j.bmcl.2005.05.129