{(1S,2R)-3-[(Benzo[1,3]dioxole-5-sulfonyl)-(6-cyano-2,2-dimethyl-hexyl)-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

Base Information

Chemical Name:{(1S,2R)-3-[(Benzo[1,3]dioxole-5-sulfonyl)-(6-cyano-2,2-dimethyl-hexyl)-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester
CAS No.:288296-37-7
Molecular Formula:C₃₃H₄₃N₃O₉S
Molecular Weight:657.785
Hs Code.:

{(1S,2R)-3-[(Benzo[1,3]dioxole-5-sulfonyl)-(6-cyano-2,2-dimethyl-hexyl)-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

Synonyms:{(1S,2R)-3-[(Benzo[1,3]dioxole-5-sulfonyl)-(6-cyano-2,2-dimethyl-hexyl)-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

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Chemical Property of {(1S,2R)-3-[(Benzo[1,3]dioxole-5-sulfonyl)-(6-cyano-2,2-dimethyl-hexyl)-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

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Technology Process of {(1S,2R)-3-[(Benzo[1,3]dioxole-5-sulfonyl)-(6-cyano-2,2-dimethyl-hexyl)-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

There total 9 articles about {(1S,2R)-3-[(Benzo[1,3]dioxole-5-sulfonyl)-(6-cyano-2,2-dimethyl-hexyl)-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester 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: 42.0%

: 151-50-8
potassium cyanide

: 681028-79-5
{(1S,2R)-3-[(Benzo[1,3]dioxole-5-sulfonyl)-(6-chloro-2,2-dimethyl-hexyl)-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

: 288296-37-7
{(1S,2R)-3-[(Benzo[1,3]dioxole-5-sulfonyl)-(6-cyano-2,2-dimethyl-hexyl)-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

Guidance literature:: In dimethyl sulfoxide; at 60 ℃;
DOI:10.1016/j.bmcl.2003.12.008

Reference yield:

: 98760-08-8,98818-34-9,98818-35-0,103127-56-6,98737-29-2
(1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester

: 288296-37-7
{(1S,2R)-3-[(Benzo[1,3]dioxole-5-sulfonyl)-(6-cyano-2,2-dimethyl-hexyl)-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

Guidance literature:: Multi-step reaction with 7 steps

1: 75 percent / aq. NaN₃ / dimethylformamide / 100 °C

2: 86 percent / TFA / CH₂Cl₂

3: 77 percent / DIEA / acetonitrile

4: 98 percent / H₂ / Pd/C / methanol / 2068.59 Torr

5: 61 percent / NaBH(OAc)3; AcOH / tetrahydrofuran

6: 88 percent / DMAP; DIEA / tetrahydrofuran

7: 42 percent / dimethylsulfoxide / 60 °C

With dmap; sodium azide; hydrogen; sodium tris(acetoxy)borohydride; acetic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/j.bmcl.2003.12.008

Reference yield:

: 162536-72-3
[R-(R*,S*)]-[3-Azido-2-hydroxy-1-(phenylmethyl) propyl]carbamic acid, 1,1-dimethylethyl ester

: 288296-37-7
{(1S,2R)-3-[(Benzo[1,3]dioxole-5-sulfonyl)-(6-cyano-2,2-dimethyl-hexyl)-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester

Guidance literature:: Multi-step reaction with 6 steps

1: 86 percent / TFA / CH₂Cl₂

2: 77 percent / DIEA / acetonitrile

3: 98 percent / H₂ / Pd/C / methanol / 2068.59 Torr

4: 61 percent / NaBH(OAc)3; AcOH / tetrahydrofuran

5: 88 percent / DMAP; DIEA / tetrahydrofuran

6: 42 percent / dimethylsulfoxide / 60 °C

With dmap; hydrogen; sodium tris(acetoxy)borohydride; acetic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; acetonitrile;
DOI:10.1016/j.bmcl.2003.12.008