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

Base Information

Chemical Name:(3R,3AS,6AR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-1-[4-(2-aminoethoxy)benzyl]-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-2-hydroxypropylcarbamate
CAS No.:313680-01-2
Molecular Formula:C₃₀H₄₁N₃O₁₀S
Molecular Weight:635.736
Hs Code.:

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

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

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

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

There total 13 articles about (3R,3AS,6AR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-1-[4-(2-aminoethoxy)benzyl]-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-2-hydroxypropylcarbamate 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: 70.0%

: 313680-00-1
(3R,3AS,6AR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-1-(4-{2-[(tert-butoxycarbonyl)amino]ethoxy}benzyl)-2-hydroxypropylcarbamate

: 313680-01-2
(3R,3AS,6AR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-1-[4-(2-aminoethoxy)benzyl]-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-2-hydroxypropylcarbamate

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2h;

Reference yield:

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

: 313680-01-2
(3R,3AS,6AR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-1-[4-(2-aminoethoxy)benzyl]-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-2-hydroxypropylcarbamate

Guidance literature:: Multi-step reaction with 7 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

6: di-t-butylazodicarboxylate; Ph₃P / CH₂Cl₂

7: TFA / CH₂Cl₂

With di-tert-butyl-diazodicarboxylate; hydrogen; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; isopropyl alcohol; acetonitrile; 6: Mitsunobu reaction;
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

: 313680-01-2
(3R,3AS,6AR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-1-[4-(2-aminoethoxy)benzyl]-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-2-hydroxypropylcarbamate

Guidance literature:: Multi-step reaction with 8 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

7: di-t-butylazodicarboxylate; Ph₃P / CH₂Cl₂

8: TFA / CH₂Cl₂

With potassium hydroxide; di-tert-butyl-diazodicarboxylate; hydrogen; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; isopropyl alcohol; acetonitrile; 7: Mitsunobu reaction;
DOI:10.1016/j.bmcl.2005.05.129