(2S,3R)-1-tert-butyldiphenylsilyloxy-3-tert-butoxycarbonylamino-2-(p-nitrobenzoyloxy)-5-hexene

Base Information

• Chemical Name: (2S,3R)-1-tert-butyldiphenylsilyloxy-3-tert-butoxycarbonylamino-2-(p-nitrobenzoyloxy)-5-hexene
• CAS No.: 905711-08-2
• Molecular Formula: C₃₄H₄₂N₂O₇Si
• Molecular Weight: 618.802
• Mol file: 905711-08-2.mol

Synonyms:(2S,3R)-1-tert-butyldiphenylsilyloxy-3-tert-butoxycarbonylamino-2-(p-nitrobenzoyloxy)-5-hexene

Chemical Property of (2S,3R)-1-tert-butyldiphenylsilyloxy-3-tert-butoxycarbonylamino-2-(p-nitrobenzoyloxy)-5-hexene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-1-tert-butyldiphenylsilyloxy-3-tert-butoxycarbonylamino-2-(p-nitrobenzoyloxy)-5-hexene

There total 1 articles about (2S,3R)-1-tert-butyldiphenylsilyloxy-3-tert-butoxycarbonylamino-2-(p-nitrobenzoyloxy)-5-hexene 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: 80.0%

(2S,3R)-1-tert-butyldiphenylsilyloxy-3-tert-butoxycarbonylamino-6-hexen-2-ol (596108-85-9) + 4-nitro-benzoic acid (62-23-7) → (2S,3R)-1-tert-butyldiphenylsilyloxy-3-tert-butoxycarbonylamino-2-(p-nitrobenzoyloxy)-5-hexene (905711-08-2)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In toluene; at 0 - 20 ℃;

DOI:10.1021/ol061022e

Reference yield: 72.0%

(2S,3R)-1-tert-butyldiphenylsilyloxy-3-tert-butoxycarbonylamino-2-(p-nitrobenzoyloxy)-5-hexene (905711-08-2) → (2S,3R)-1-tert-butyldiphenylsilyloxy-3-tert-butoxycarbonylamino-5-hexen-2-ol (905711-09-3)

Guidance literature:

With sodium bis(2-methoxyethoxy)aluminium dihydride; In diethyl ether; at -20 ℃; for 6h;

DOI:10.1021/ol061022e

Reference yield:

(2S,3R)-1-tert-butyldiphenylsilyloxy-3-tert-butoxycarbonylamino-2-(p-nitrobenzoyloxy)-5-hexene (905711-08-2) → (4R,5S)-4-allyl-5-tert-butyldiphenylsilyloxymethyl-3-tert-butoxycarbonyl-2,2-dimethyl-oxazolidine (905711-10-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / RedAl(R) / diethyl ether / 6 h / -20 °C

2: 70 percent / p-toluenesulfonic acid / toluene / 4.5 h / 85 °C

With toluene-4-sulfonic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; In diethyl ether; toluene;

DOI:10.1021/ol061022e

upstream raw materials:

(2S,3R)-1-tert-butyldiphenylsilyloxy-3-tert-butoxycarbonylamino-6-hexen-2-ol

4-nitro-benzoic acid

Downstream raw materials:

(2S,3R)-1-tert-butyldiphenylsilyloxy-3-tert-butoxycarbonylamino-5-hexen-2-ol

(4R,5S)-4-allyl-5-tert-butyldiphenylsilyloxymethyl-3-tert-butoxycarbonyl-2,2-dimethyl-oxazolidine