[(1R)-2-methyl-1-[[(3aR,6S,7aS)-tetrahydro-8,8-dimethyl-2,2-dioxide-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]carbonyl]propyl]carbamic acid 2,2-dioxide phenylmethyl ester

Base Information

• Chemical Name: [(1R)-2-methyl-1-[[(3aR,6S,7aS)-tetrahydro-8,8-dimethyl-2,2-dioxide-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]carbonyl]propyl]carbamic acid 2,2-dioxide phenylmethyl ester
• CAS No.: 261165-25-7
• Molecular Formula: C₂₃H₃₂N₂O₅S
• Molecular Weight: 448.583
• Mol file: 261165-25-7.mol

Synonyms:[(1R)-2-methyl-1-[[(3aR,6S,7aS)-tetrahydro-8,8-dimethyl-2,2-dioxide-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]carbonyl]propyl]carbamic acid 2,2-dioxide phenylmethyl ester

Chemical Property of [(1R)-2-methyl-1-[[(3aR,6S,7aS)-tetrahydro-8,8-dimethyl-2,2-dioxide-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]carbonyl]propyl]carbamic acid 2,2-dioxide phenylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(1R)-2-methyl-1-[[(3aR,6S,7aS)-tetrahydro-8,8-dimethyl-2,2-dioxide-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]carbonyl]propyl]carbamic acid 2,2-dioxide phenylmethyl ester

There total 6 articles about [(1R)-2-methyl-1-[[(3aR,6S,7aS)-tetrahydro-8,8-dimethyl-2,2-dioxide-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]carbonyl]propyl]carbamic acid 2,2-dioxide phenylmethyl 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: 92.0%

benzyl chloroformate (501-53-1,94274-21-2) + (R)-2-Amino-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3-methyl-butan-1-one (261168-61-0) → [(1R)-2-methyl-1-[[(3aR,6S,7aS)-tetrahydro-8,8-dimethyl-2,2-dioxide-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]carbonyl]propyl]carbamic acid 2,2-dioxide phenylmethyl ester (261165-25-7)

Guidance literature:

With sodium carbonate; In acetone; at 0 ℃;

DOI:10.1039/b203493j

Reference yield:

((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-oxo-acetaldehyde O-benzyl-oxime → [(1R)-2-methyl-1-[[(3aR,6S,7aS)-tetrahydro-8,8-dimethyl-2,2-dioxide-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]carbonyl]propyl]carbamic acid 2,2-dioxide phenylmethyl ester (261165-25-7)

Guidance literature:

Multi-step reaction with 3 steps

1: indium / H₂O / 48 h / 20 °C

2: 77 percent / H₂ / Pd(OH)2 / methanol / 20 °C

3: 92 percent / aq. Na₂CO₃ / acetone / 0 °C

With indium; hydrogen; sodium carbonate; palladium dihydroxide; In methanol; water; acetone;

DOI:10.1039/b203493j

Reference yield:

(R)-2-Benzyloxyamino-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-3-methyl-butan-1-one (261165-24-6) → [(1R)-2-methyl-1-[[(3aR,6S,7aS)-tetrahydro-8,8-dimethyl-2,2-dioxide-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]carbonyl]propyl]carbamic acid 2,2-dioxide phenylmethyl ester (261165-25-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / H₂ / Pd(OH)2 / methanol / 20 °C

2: 92 percent / aq. Na₂CO₃ / acetone / 0 °C

With hydrogen; sodium carbonate; palladium dihydroxide; In methanol; acetone;

DOI:10.1039/b203493j

upstream raw materials:

benzyl chloroformate

(R)-2-Amino-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-methyl-butan-1-one

(3aR,6S,7aS)-hexahydro-8,8-dimethyl-1-[(2R)-1-oxo-2-(2,2-diphenylhydrazino)-3-(methyl)butyl]-3H-3a,6-methano-2,1-benzisothiazole 2,2-dioxide

(+)-camphorsultam

Downstream raw materials:

N-[(benzyloxy)carbonyl]-D-valine

Refernces

• 1、 Ueda, Masafumi,Miyabe, Hideto,Sugino, Hisako,Naito, Takeaki. "Zinc-mediated carbon radical addition to glyoxylic imines in aqueous media for the synthesis of α-amino acids". . p. 1124 - 1128. Retrieved 2007/10/03.