(2S,3S)-3-tert-butoxycarbonylamino-4-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-1,2,4-butanetriol

Base Information

• Chemical Name: (2S,3S)-3-tert-butoxycarbonylamino-4-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-1,2,4-butanetriol
• CAS No.: 136537-05-8
• Molecular Formula: C₂₈H₄₁NO₅Si
• Molecular Weight: 499.723
• Mol file: 136537-05-8.mol

Synonyms:(2S,3S)-3-tert-butoxycarbonylamino-4-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-1,2,4-butanetriol

Chemical Property of (2S,3S)-3-tert-butoxycarbonylamino-4-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-1,2,4-butanetriol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-3-tert-butoxycarbonylamino-4-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-1,2,4-butanetriol

There total 7 articles about (2S,3S)-3-tert-butoxycarbonylamino-4-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-1,2,4-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: 92.0%

di-tert-butyl dicarbonate (24424-99-5) + (2S,3S)-3-amino-4-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-1,2,4-butanetriol (136537-04-7) → (2S,3S)-3-tert-butoxycarbonylamino-4-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-1,2,4-butanetriol (136537-05-8)

Guidance literature:

In dichloromethane; for 1h; Ambient temperature;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (2S,3S)-3-tert-butoxycarbonylamino-4-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-1,2,4-butanetriol (136537-05-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / H₂ / Pd/C / methanol / 20 °C

2: 100 percent / lithium aluminium hydride / tetrahydrofuran / 20 °C

3: 90 percent / imidazole / CH₂Cl₂ / 20 °C

With 1H-imidazole; lithium aluminium tetrahydride; hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1002/ejoc.200400734

Reference yield:

(R)-(Benzyl-methoxycarbonylmethoxy-amino)-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-acetic acid methyl ester (851959-90-5) → (2S,3S)-3-tert-butoxycarbonylamino-4-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-1,2,4-butanetriol (136537-05-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / H₂ / Pd/C / methanol / 20 °C

2: 100 percent / lithium aluminium hydride / tetrahydrofuran / 20 °C

3: 90 percent / imidazole / CH₂Cl₂ / 20 °C

With 1H-imidazole; lithium aluminium tetrahydride; hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1002/ejoc.200400734

upstream raw materials:

di-tert-butyl dicarbonate

(2S,3S)-3-amino-4-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-1,2,4-butanetriol

methyl (2R)-2-[(tert-butylcarbonyl)amino]-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanoate

(R)-(Benzyl-methoxycarbonylmethoxy-amino)-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-acetic acid methyl ester

Downstream raw materials:

(2S,3S)-2-tert-butoxycarbonylamino-1-O-tert-butyldiphenylsilyl-3,4-epoxy-1-butanol

Toluene-4-sulfonic acid (2S,3S)-3-tert-butoxycarbonylamino-4-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-butyl ester

(Z)-(2S,3R)-2-Amino-1-(tert-butyl-diphenyl-silanyloxy)-octadec-8-en-3-ol; compound with trifluoro-acetic acid

(E)-(2S,3R)-2-Amino-1-(tert-butyl-diphenyl-silanyloxy)-octadec-8-en-3-ol; compound with trifluoro-acetic acid