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

Base Information

• Chemical Name: (2S,3R)-N⁽²⁾-(tert-butoxycarbonyl)-O⁽³⁾-benzoyl-O⁽⁴⁾-(tert-butyldimethylsilyl)-2-amino-1,3,4-butanetriol
• CAS No.: 371257-96-4
• Molecular Formula: C₂₂H₃₇NO₆Si
• Molecular Weight: 439.624

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

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

Chemical Property:

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

There total 9 articles about (2S,3R)-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: 87.0%

(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) → (2S,3R)-N(2)-(tert-butoxycarbonyl)-O(3)-benzoyl-O(4)-(tert-butyldimethylsilyl)-2-amino-1,3,4-butanetriol (371257-96-4)

Guidance literature:

With hydrogen; palladium on activated charcoal;

DOI:10.1016/S0040-4039(01)02206-7

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (2S,3R)-N(2)-(tert-butoxycarbonyl)-O(3)-benzoyl-O(4)-(tert-butyldimethylsilyl)-2-amino-1,3,4-butanetriol (371257-96-4)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 87 percent / H₂ / Pd/C / ethanol / 3102.97 Torr

With dmap; hydrogen; palladium on activated charcoal; In tetrahydrofuran; ethanol; chloroform;

DOI:10.1021/jo015886j

Reference yield:

(4R,5R)-4,5-di(isopropyloxycarbonyl)-3-benzoyloxazolidin-2-one (253350-02-6) → (2S,3R)-N(2)-(tert-butoxycarbonyl)-O(3)-benzoyl-O(4)-(tert-butyldimethylsilyl)-2-amino-1,3,4-butanetriol (371257-96-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 89 percent / BF₃*OEt₂ / propan-2-ol / Heating

2.1: BF₃*OEt₂ / tetrahydrofuran / 4 h

2.2: 92 percent / NaBH₄ / tetrahydrofuran / 120 h / 20 °C

3.1: 90 percent / triflic acid / CH₂Cl₂; tetrahydrofuran / 48 h / 20 °C

4.1: 93 percent / NaBH₄ / tetrahydrofuran / 24 h / 20 °C

5.1: 82 percent / imidazole / dimethylformamide / 20 °C

6.1: 94 percent / DMAP / CHCl₃ / 1 h / 20 °C

7.1: 78 percent / tetrahydrofuran / 0.17 h / -78 °C

8.1: 87 percent / H₂ / Pd/C / ethanol / 3102.97 Torr

With 1H-imidazole; dmap; sodium tetrahydroborate; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; hydrogen; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1021/jo015886j

upstream raw materials:

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

di-tert-butyl dicarbonate

(4R,5R)-4,5-di(isopropyloxycarbonyl)-3-benzoyloxazolidin-2-one

(4S,5R)-4-hydroxymethyl-5-(isopropyloxycarbonyl)oxazolidin-2-one

Downstream raw materials:

benzoic acid 2-tert-butoxycarbonylamino-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-(toluene-4-sulfonyloxy)-propyl ester

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

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

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

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