N-(tert-butoxycarbonyl)-O-<(4-methoxyphenyl)diphenylmethyl>-trans-4-hydroxy-D-prolinol

Base Information

• Chemical Name: N-(tert-butoxycarbonyl)-O-<(4-methoxyphenyl)diphenylmethyl>-trans-4-hydroxy-D-prolinol
• CAS No.: 135042-21-6
• Molecular Formula: C₃₀H₃₅NO₅
• Molecular Weight: 489.612
• Mol file: 135042-21-6.mol

Synonyms:N-(tert-butoxycarbonyl)-O-<(4-methoxyphenyl)diphenylmethyl>-trans-4-hydroxy-D-prolinol

Chemical Property of N-(tert-butoxycarbonyl)-O-<(4-methoxyphenyl)diphenylmethyl>-trans-4-hydroxy-D-prolinol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(tert-butoxycarbonyl)-O-<(4-methoxyphenyl)diphenylmethyl>-trans-4-hydroxy-D-prolinol

There total 6 articles about N-(tert-butoxycarbonyl)-O-<(4-methoxyphenyl)diphenylmethyl>-trans-4-hydroxy-D-prolinol 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: 87.7%

(2R,4S)-tert-butyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate (77450-03-4) + mono-4-methoxytrityl chloride (14470-28-1) → N-(tert-butoxycarbonyl)-O-<(4-methoxyphenyl)diphenylmethyl>-trans-4-hydroxy-D-prolinol (135042-21-6)

Guidance literature:

With triethylamine; In tetrahydrofuran; dichloromethane; for 43h; Ambient temperature;

DOI:10.1021/jm00113a017

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → N-(tert-butoxycarbonyl)-O-<(4-methoxyphenyl)diphenylmethyl>-trans-4-hydroxy-D-prolinol (135042-21-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 82.5 percent / aq. NaOH / tetrahydrofuran / Ambient temperature

2: 92.4 percent / dioxane; diethyl ether / 0.25 h / 5 °C

3: 93.9 percent / Ph₃P, DEAD / tetrahydrofuran / 42 h / Ambient temperature

4: 97.4 percent / LiBH₄ / tetrahydrofuran / Ambient temperature

5: 87.7 percent / Et₃N / CH₂Cl₂; tetrahydrofuran / 43 h / Ambient temperature

With sodium hydroxide; lithium borohydride; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane;

DOI:10.1021/jm00113a017

Reference yield:

(2R,4R)-1-tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate (114676-69-6) → N-(tert-butoxycarbonyl)-O-<(4-methoxyphenyl)diphenylmethyl>-trans-4-hydroxy-D-prolinol (135042-21-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 93.9 percent / Ph₃P, DEAD / tetrahydrofuran / 42 h / Ambient temperature

2: 97.4 percent / LiBH₄ / tetrahydrofuran / Ambient temperature

3: 87.7 percent / Et₃N / CH₂Cl₂; tetrahydrofuran / 43 h / Ambient temperature

With lithium borohydride; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm00113a017

upstream raw materials:

(2R,4S)-tert-butyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate

mono-4-methoxytrityl chloride

di-tert-butyl dicarbonate

(4R)-1-(tert-butoxycarbonyl)-4-hydroxy-D-proline

Downstream raw materials:

N-(tert-butoxycarbonyl)-O-<(4-methoxyphenyl)diphenylmethyl>-cis-4-(6-chloro-9H-purin-9-yl)-D-prolinol

N-(tert-butoxycarbonyl)-O-<(4-methoxyphenyl)diphenylmethyl>-cis-4-(2-amino-6-chloro-9H-purin-9-yl)-D-prolinol

(3R,5R)-2-amino-1,9-dihydro-9-<5-(hydroxymethyl)-3-pyrrolidinyl>-6H-purin-6-one

N-(tert-butoxycarbonyl)-O-<(4-methoxyphenyl)diphenylmethyl>-cis-4-(2,6-diamino-9H-purin-9-yl)-D-prolinol