{(1S,2R)-3-[(Benzo[1,3]dioxole-5-sulfonyl)-(5-cyano-2,2-dimethyl-pentyl)-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid tert-butyl ester

Base Information

• Chemical Name: {(1S,2R)-3-[(Benzo[1,3]dioxole-5-sulfonyl)-(5-cyano-2,2-dimethyl-pentyl)-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid tert-butyl ester
• CAS No.: 681028-81-9
• Molecular Formula: C₃₀H₄₁N₃O₇S
• Molecular Weight: 587.737

Synonyms:{(1S,2R)-3-[(Benzo[1,3]dioxole-5-sulfonyl)-(5-cyano-2,2-dimethyl-pentyl)-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid tert-butyl ester

Chemical Property of {(1S,2R)-3-[(Benzo[1,3]dioxole-5-sulfonyl)-(5-cyano-2,2-dimethyl-pentyl)-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid tert-butyl ester

Chemical Property:

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Technology Process of {(1S,2R)-3-[(Benzo[1,3]dioxole-5-sulfonyl)-(5-cyano-2,2-dimethyl-pentyl)-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid tert-butyl ester

There total 5 articles about {(1S,2R)-3-[(Benzo[1,3]dioxole-5-sulfonyl)-(5-cyano-2,2-dimethyl-pentyl)-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid tert-butyl 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:

(1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester (98760-08-8,98818-34-9,98818-35-0,103127-56-6,98737-29-2) → {(1S,2R)-3-[(Benzo[1,3]dioxole-5-sulfonyl)-(5-cyano-2,2-dimethyl-pentyl)-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid tert-butyl ester (681028-81-9)

Guidance literature:

Multi-step reaction with 4 steps

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

2: 98 percent / H₂ / Pd/C / methanol / 2068.59 Torr

3: 55 percent / NaBH(OAc)3; AcOH / dimethylformamide; tetrahydrofuran

4: 86 percent / DMAP; DIEA / tetrahydrofuran

With dmap; sodium azide; hydrogen; sodium tris(acetoxy)borohydride; acetic acid; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2003.12.008

Reference yield:

5-chloro-2,2-dimethylpentanal (52387-40-3) → {(1S,2R)-3-[(Benzo[1,3]dioxole-5-sulfonyl)-(5-cyano-2,2-dimethyl-pentyl)-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid tert-butyl ester (681028-81-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 75 percent / PTSA / toluene / Heating

2: 85 percent / dimethylsulfoxide / 18 h / 100 °C

3: aq. HCl / tetrahydrofuran / 4.5 h / 70 °C

4: 55 percent / NaBH(OAc)3; AcOH / dimethylformamide; tetrahydrofuran

5: 86 percent / DMAP; DIEA / tetrahydrofuran

With hydrogenchloride; dmap; sodium tris(acetoxy)borohydride; toluene-4-sulfonic acid; acetic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.bmcl.2003.12.008

Reference yield:

5,5-Dimethyl-6-oxo-hexanenitrile (87921-72-0) → {(1S,2R)-3-[(Benzo[1,3]dioxole-5-sulfonyl)-(5-cyano-2,2-dimethyl-pentyl)-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid tert-butyl ester (681028-81-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 55 percent / NaBH(OAc)3; AcOH / dimethylformamide; tetrahydrofuran

2: 86 percent / DMAP; DIEA / tetrahydrofuran

With dmap; sodium tris(acetoxy)borohydride; acetic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2003.12.008

upstream raw materials:

5-chloro-2,2-dimethylpentanal

(1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester

5,5-Dimethyl-6-oxo-hexanenitrile

(1S,2R)-(3-amino-1-benzyl-2-hydroxy-propyl)-carbamic acid tert butyl ester

Downstream raw materials:

(3R,3aS,6aR)-hexahydro[2,3-b]furan-3-yl N-((1S,2R)-1-benzyl-3-[6-amino-2,2-dimethylhexyl][(3,4-methylenedioxyphenyl)sulfonyl]amino-2-hydroxypropyl)carbamate

(3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl N-(1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl)(5-cyano-2,2-dimethylpentyl)amino]-1-benzyl-2-hydroxypropylcarbamate

Benzo[1,3]dioxole-5-sulfonic acid ((2R,3S)-3-amino-2-hydroxy-4-phenyl-butyl)-(5-cyano-2,2-dimethyl-pentyl)-amide

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