(R)-2-(2,2,2-Trichloro-ethoxycarbonylamino)-3-tritylsulfanyl-propionic acid (5R,7R,10R)-11-allyloxy-2,2,12-trimethyl-5,6,7,10-tetrahydro-4H-1,3,15,17-tetraoxa-6-aza-cyclopenta[a]phenanthren-7-ylmethyl ester

Base Information

• Chemical Name: (R)-2-(2,2,2-Trichloro-ethoxycarbonylamino)-3-tritylsulfanyl-propionic acid (5R,7R,10R)-11-allyloxy-2,2,12-trimethyl-5,6,7,10-tetrahydro-4H-1,3,15,17-tetraoxa-6-aza-cyclopenta[a]phenanthren-7-ylmethyl ester
• CAS No.: 654644-03-8
• Molecular Formula: C₄₄H₄₅Cl₃N₂O₉S
• Molecular Weight: 884.274
• Mol file: 654644-03-8.mol

Synonyms:(R)-2-(2,2,2-Trichloro-ethoxycarbonylamino)-3-tritylsulfanyl-propionic acid (5R,7R,10R)-11-allyloxy-2,2,12-trimethyl-5,6,7,10-tetrahydro-4H-1,3,15,17-tetraoxa-6-aza-cyclopenta[a]phenanthren-7-ylmethyl ester

Chemical Property of (R)-2-(2,2,2-Trichloro-ethoxycarbonylamino)-3-tritylsulfanyl-propionic acid (5R,7R,10R)-11-allyloxy-2,2,12-trimethyl-5,6,7,10-tetrahydro-4H-1,3,15,17-tetraoxa-6-aza-cyclopenta[a]phenanthren-7-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-(2,2,2-Trichloro-ethoxycarbonylamino)-3-tritylsulfanyl-propionic acid (5R,7R,10R)-11-allyloxy-2,2,12-trimethyl-5,6,7,10-tetrahydro-4H-1,3,15,17-tetraoxa-6-aza-cyclopenta[a]phenanthren-7-ylmethyl ester

There total 14 articles about (R)-2-(2,2,2-Trichloro-ethoxycarbonylamino)-3-tritylsulfanyl-propionic acid (5R,7R,10R)-11-allyloxy-2,2,12-trimethyl-5,6,7,10-tetrahydro-4H-1,3,15,17-tetraoxa-6-aza-cyclopenta[a]phenanthren-7-ylmethyl 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: 87.0%

(R)-N-2,2,2-trichloroethoxycarbonyl-(S-trityl)cysteine (96845-11-3) + (11-allyloxy-2,2,12-trimethyl-5,6,7,10-tetrahydro-4H-1,3,15,17-tetraoxa-6-aza-cyclopenta[a]phenanthren-7-yl)-methanol (654643-96-6) → (R)-2-(2,2,2-Trichloro-ethoxycarbonylamino)-3-tritylsulfanyl-propionic acid (5R,7R,10R)-11-allyloxy-2,2,12-trimethyl-5,6,7,10-tetrahydro-4H-1,3,15,17-tetraoxa-6-aza-cyclopenta[a]phenanthren-7-ylmethyl ester (654644-03-8)

Guidance literature:

With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 6h;

DOI:10.1021/jo050408k

Reference yield:

[(1R,2R)-2-(6-Allyloxy-7-methyl-benzo[1,3]dioxol-5-yl)-2-hydroxy-1-hydroxymethyl-ethyl]-carbamic acid tert-butyl ester (426213-78-7) → (R)-2-(2,2,2-Trichloro-ethoxycarbonylamino)-3-tritylsulfanyl-propionic acid (5R,7R,10R)-11-allyloxy-2,2,12-trimethyl-5,6,7,10-tetrahydro-4H-1,3,15,17-tetraoxa-6-aza-cyclopenta[a]phenanthren-7-ylmethyl ester (654644-03-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.5 g / p-TsOH / dimethylformamide / 6 h

2: 90 percent / 2,6-lutidine; tert-butyldimethylsilyl triflate / CH₂Cl₂ / -78 - 20 °C

3: 85 percent / LiCl; molecular sieves 4 Angstroem / toluene; various solvent(s) / 48 h / 20 °C

4: 98 percent / NaHCO₃ / CH₂Cl₂ / 2 h / 20 °C

5: DBU / tetrahydrofuran / 14 h / 20 °C

6: 205.0 mg / Zn; AcOH / diethyl ether / 1 h / 20 °C

7: 90 percent / LiAlH₄ / tetrahydrofuran / 2.5 h / -20 - 0 °C

8: 87 percent / DMAP; HOBt; EDCl / CH₂Cl₂ / 6 h / 20 °C

With 2,6-dimethylpyridine; dmap; lithium aluminium tetrahydride; 4 A molecular sieve; t-butyldimethylsiyl triflate; sodium hydrogencarbonate; benzotriazol-1-ol; toluene-4-sulfonic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium chloride; zinc; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; 3: Pictet-Spengler reaction;

DOI:10.1021/jo050408k

Reference yield:

5-methoxy methoxy-4-methyl benzo[d][1,3]dioxole (187040-02-4) → (R)-2-(2,2,2-Trichloro-ethoxycarbonylamino)-3-tritylsulfanyl-propionic acid (5R,7R,10R)-11-allyloxy-2,2,12-trimethyl-5,6,7,10-tetrahydro-4H-1,3,15,17-tetraoxa-6-aza-cyclopenta[a]phenanthren-7-ylmethyl ester (654644-03-8)

Guidance literature:

Multi-step reaction with 12 steps

1: 85 percent / NaI; TMSCl / acetonitrile / 2 h / -30 °C

2: 98 percent / MeMgCl / tetrahydrofuran; CH₂Cl₂ / 20 °C

3: NaI; Cs₂CO₃ / dimethylformamide / 3 h / 20 °C

4: p-TsOH / methanol / 1 h / 0 °C

5: 1.5 g / p-TsOH / dimethylformamide / 6 h

6: 90 percent / 2,6-lutidine; tert-butyldimethylsilyl triflate / CH₂Cl₂ / -78 - 20 °C

7: 85 percent / LiCl; molecular sieves 4 Angstroem / toluene; various solvent(s) / 48 h / 20 °C

8: 98 percent / NaHCO₃ / CH₂Cl₂ / 2 h / 20 °C

9: DBU / tetrahydrofuran / 14 h / 20 °C

10: 205.0 mg / Zn; AcOH / diethyl ether / 1 h / 20 °C

11: 90 percent / LiAlH₄ / tetrahydrofuran / 2.5 h / -20 - 0 °C

12: 87 percent / DMAP; HOBt; EDCl / CH₂Cl₂ / 6 h / 20 °C

With 2,6-dimethylpyridine; dmap; lithium aluminium tetrahydride; chloro-trimethyl-silane; 4 A molecular sieve; t-butyldimethylsiyl triflate; methylmagnesium chloride; sodium hydrogencarbonate; benzotriazol-1-ol; caesium carbonate; toluene-4-sulfonic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium iodide; lithium chloride; zinc; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 7: Pictet-Spengler reaction;

DOI:10.1021/jo050408k

upstream raw materials:

(R)-N-2,2,2-trichloroethoxycarbonyl-(S-trityl)cysteine

(11-allyloxy-2,2,12-trimethyl-5,6,7,10-tetrahydro-4H-1,3,15,17-tetraoxa-6-aza-cyclopenta[a]phenanthren-7-yl)-methanol

5-methoxy methoxy-4-methyl benzo[d][1,3]dioxole

4-methylbenzo[1,3]dioxol-5-ol

Downstream raw materials:

C₄₁H₃₉Cl₃N₂O₈S