(2S,3R)-O⁽¹⁾-benzyl-N⁽²⁾-(tert-butoxycarbonyl)-O⁽³⁾-benzoyl-O⁽⁴⁾-(tert-butyldimethylsilyl)-2-amino-1,3,4-butanetriol

Base Information

• Chemical Name: (2S,3R)-O⁽¹⁾-benzyl-N⁽²⁾-(tert-butoxycarbonyl)-O⁽³⁾-benzoyl-O⁽⁴⁾-(tert-butyldimethylsilyl)-2-amino-1,3,4-butanetriol
• CAS No.: 371257-94-2
• Molecular Formula: C₂₉H₄₃NO₆Si
• Molecular Weight: 529.749

Synonyms:(2S,3R)-O⁽¹⁾-benzyl-N⁽²⁾-(tert-butoxycarbonyl)-O⁽³⁾-benzoyl-O⁽⁴⁾-(tert-butyldimethylsilyl)-2-amino-1,3,4-butanetriol

Chemical Property of (2S,3R)-O⁽¹⁾-benzyl-N⁽²⁾-(tert-butoxycarbonyl)-O⁽³⁾-benzoyl-O⁽⁴⁾-(tert-butyldimethylsilyl)-2-amino-1,3,4-butanetriol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (2S,3R)-O⁽¹⁾-benzyl-N⁽²⁾-(tert-butoxycarbonyl)-O⁽³⁾-benzoyl-O⁽⁴⁾-(tert-butyldimethylsilyl)-2-amino-1,3,4-butanetriol

There total 9 articles about (2S,3R)-O⁽¹⁾-benzyl-N⁽²⁾-(tert-butoxycarbonyl)-O⁽³⁾-benzoyl-O⁽⁴⁾-(tert-butyldimethylsilyl)-2-amino-1,3,4-butanetriol 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: 78.0%

phenyllithium (591-51-5) + (4S,5R)-4-benzyloxymethyl-3-(tert-butoxycarbonyl)-5-(tert-butyldimethylsilyloxymethyl)oxazolidin-2-one (371257-92-0) → (2S,3R)-O(1)-benzyl-N(2)-(tert-butoxycarbonyl)-O(3)-benzoyl-O(4)-(tert-butyldimethylsilyl)-2-amino-1,3,4-butanetriol (371257-94-2)

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 0.166667h;

DOI:10.1021/jo015886j

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (2S,3R)-O(1)-benzyl-N(2)-(tert-butoxycarbonyl)-O(3)-benzoyl-O(4)-(tert-butyldimethylsilyl)-2-amino-1,3,4-butanetriol (371257-94-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / DMAP / CHCl₃ / 1 h / 20 °C

2: 78 percent / tetrahydrofuran / 0.17 h / -78 °C

With dmap; In tetrahydrofuran; chloroform;

DOI:10.1021/jo015886j

Reference yield:

O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) → (2S,3R)-O(1)-benzyl-N(2)-(tert-butoxycarbonyl)-O(3)-benzoyl-O(4)-(tert-butyldimethylsilyl)-2-amino-1,3,4-butanetriol (371257-94-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / triflic acid / CH₂Cl₂; tetrahydrofuran / 48 h / 20 °C

2: 93 percent / NaBH₄ / tetrahydrofuran / 24 h / 20 °C

3: 82 percent / imidazole / dimethylformamide / 20 °C

4: 94 percent / DMAP / CHCl₃ / 1 h / 20 °C

5: 78 percent / tetrahydrofuran / 0.17 h / -78 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; trifluorormethanesulfonic acid; In tetrahydrofuran; dichloromethane; chloroform; N,N-dimethyl-formamide;

DOI:10.1021/jo015886j

upstream raw materials:

phenyllithium

(4S,5R)-4-benzyloxymethyl-3-(tert-butoxycarbonyl)-5-(tert-butyldimethylsilyloxymethyl)oxazolidin-2-one

di-tert-butyl dicarbonate

O-benzyl 2,2,2-trichloroacetimidate

Downstream raw materials:

(2S,3R)-N⁽²⁾-(tert-butoxycarbonyl)-O⁽³⁾-benzoyl-O⁽⁴⁾-(tert-butyldimethylsilyl)-2-amino-1,3,4-butanetriol

2-[1-benzoyloxy-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-aziridine-1-carboxylic acid tert-butyl ester

benzoic acid 2-tert-butoxycarbonylamino-1-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-pentyl ester

Benzoic acid (1R,2S)-2-tert-butoxycarbonylamino-4-methyl-1-(toluene-4-sulfonyloxymethyl)-pentyl ester

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