(1S,3R,2'R)-2-benzyl-1-[2'-benzyloxycarbonyl-2'-(tert-butoxycarbonyl)aminoethyl]-3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline

Base Information

• Chemical Name: (1S,3R,2'R)-2-benzyl-1-[2'-benzyloxycarbonyl-2'-(tert-butoxycarbonyl)aminoethyl]-3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline
• CAS No.: 305322-27-4
• Molecular Formula: C₃₅H₃₉N₃O₆
• Molecular Weight: 597.711
• Mol file: 305322-27-4.mol

Synonyms:(1S,3R,2'R)-2-benzyl-1-[2'-benzyloxycarbonyl-2'-(tert-butoxycarbonyl)aminoethyl]-3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline

Chemical Property of (1S,3R,2'R)-2-benzyl-1-[2'-benzyloxycarbonyl-2'-(tert-butoxycarbonyl)aminoethyl]-3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3R,2'R)-2-benzyl-1-[2'-benzyloxycarbonyl-2'-(tert-butoxycarbonyl)aminoethyl]-3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline

There total 4 articles about (1S,3R,2'R)-2-benzyl-1-[2'-benzyloxycarbonyl-2'-(tert-butoxycarbonyl)aminoethyl]-3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline 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: 68.0%

D-(+)-Nbbenzyltryptophan methyl ester (63229-68-5,73327-10-3,84094-71-3) + Boc-D-Asp(H)-OBzl (134676-02-1) → (1S,3R,2'R)-2-benzyl-1-[2'-benzyloxycarbonyl-2'-(tert-butoxycarbonyl)aminoethyl]-3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline (305322-27-4)

Guidance literature:

With trifluoroacetic acid; In toluene; at 20 ℃;

DOI:10.1021/jm000959x

Reference yield:

(R)-2-tert-butoxycarbonylamino-succinic acid 1-benzyl ester (92828-64-3) → (1S,3R,2'R)-2-benzyl-1-[2'-benzyloxycarbonyl-2'-(tert-butoxycarbonyl)aminoethyl]-3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline (305322-27-4)

Guidance literature:

Multi-step reaction with 4 steps

1: NMM / tetrahydrofuran / 0.17 h / -15 °C

2: NaBH₄ / H₂O / -10 °C

3: 84 percent / (COCl)2; DMSO / CH₂Cl₂ / 0.5 h / -60 °C

4: 68 percent / TFA / toluene / 20 °C

With 4-methyl-morpholine; sodium tetrahydroborate; oxalyl dichloride; dimethyl sulfoxide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; toluene;

DOI:10.1021/jm000959x

Reference yield:

(R)-2-tert-Butoxycarbonylamino-4-isobutoxycarbonyloxy-4-oxo-butyric acid benzyl ester → (1S,3R,2'R)-2-benzyl-1-[2'-benzyloxycarbonyl-2'-(tert-butoxycarbonyl)aminoethyl]-3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline (305322-27-4)

Guidance literature:

Multi-step reaction with 3 steps

1: NaBH₄ / H₂O / -10 °C

2: 84 percent / (COCl)2; DMSO / CH₂Cl₂ / 0.5 h / -60 °C

3: 68 percent / TFA / toluene / 20 °C

With sodium tetrahydroborate; oxalyl dichloride; dimethyl sulfoxide; trifluoroacetic acid; In dichloromethane; water; toluene;

DOI:10.1021/jm000959x

upstream raw materials:

D-(+)-N_bbenzyltryptophan methyl ester

Boc-D-Asp(H)-OBzl

(R)-2-tert-butoxycarbonylamino-succinic acid 1-benzyl ester

benzyl (2R)-(tert-butoxycarbonyl)amino-4-hydroxybutanoate

Downstream raw materials:

(2R,5R,11bS)-2-(benzyloxycarbonyl)amino-5-methoxycarbonyl-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole

(2R,5R,11bS)-2-(benzyloxycarbonyl)amino-5-carboxy-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole

(2R,5R,11bS,1'S)-2-(tert-butoxycarbonyl)amino-5-(1'-methoxycarbonyl-2'-phenylethyl)carbamoyl-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole

(S)-2-[((2R,5R,11bS)-2-Benzyloxycarbonylamino-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole-5-carbonyl)-amino]-3-phenyl-propionic acid methyl ester