tert-butyl (2R,3S)-[3-(benzyloxy)-1-oxopent-4-en-2-yl]carbamate

Base Information

• Chemical Name: tert-butyl (2R,3S)-[3-(benzyloxy)-1-oxopent-4-en-2-yl]carbamate
• CAS No.: 1277172-62-9
• Molecular Formula: C₁₇H₂₃NO₄
• Molecular Weight: 305.374
• Mol file: 1277172-62-9.mol

Synonyms:tert-butyl (2R,3S)-[3-(benzyloxy)-1-oxopent-4-en-2-yl]carbamate

Chemical Property of tert-butyl (2R,3S)-[3-(benzyloxy)-1-oxopent-4-en-2-yl]carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (2R,3S)-[3-(benzyloxy)-1-oxopent-4-en-2-yl]carbamate

There total 10 articles about tert-butyl (2R,3S)-[3-(benzyloxy)-1-oxopent-4-en-2-yl]carbamate 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: 70.0%

(1S,2S)-(2-benzyloxy-1-hydroxymethyl-but-3-enyl)-carbamic acid tert-butyl ester (1042338-99-7) → tert-butyl (2R,3S)-[3-(benzyloxy)-1-oxopent-4-en-2-yl]carbamate (1277172-62-9)

Guidance literature:

With pyridine; chromium(VI) oxide; acetic anhydride; In dichloromethane; at 0 ℃; for 0.333333h;

DOI:10.1002/ejoc.201001171

Reference yield:

tert-butyl (2S,3S)-[3-(benzyloxy)-1-(trityloxy)pent-4-en-2-yl]carbamate (1277172-61-8) → tert-butyl (2R,3S)-[3-(benzyloxy)-1-oxopent-4-en-2-yl]carbamate (1277172-62-9)

Guidance literature:

Multi-step reaction with 2 steps

1: perchloric acid / methanol / 4 h / 20 °C

2: pyridine; chromium(VI) oxide; acetic anhydride / dichloromethane / 0.33 h / 0 °C

With pyridine; chromium(VI) oxide; perchloric acid; acetic anhydride; In methanol; dichloromethane;

DOI:10.1002/ejoc.201001171

Reference yield:

(2R,3S)-3-(benzyloxy)-1-(trityloxy)pent-4-en-2-yl methanesulfonate (1277172-59-4) → tert-butyl (2R,3S)-[3-(benzyloxy)-1-oxopent-4-en-2-yl]carbamate (1277172-62-9)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium azide / N,N-dimethyl-formamide / 6 h / 120 °C

2: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / 0 - 20 °C

3: sodium hydrogencarbonate / ethyl acetate / 4 h / 0 °C

4: perchloric acid / methanol / 4 h / 20 °C

5: pyridine; chromium(VI) oxide; acetic anhydride / dichloromethane / 0.33 h / 0 °C

With pyridine; chromium(VI) oxide; lithium aluminium tetrahydride; sodium azide; perchloric acid; acetic anhydride; sodium hydrogencarbonate; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.201001171

upstream raw materials:

(1S,2S)-(2-benzyloxy-1-hydroxymethyl-but-3-enyl)-carbamic acid tert-butyl ester

(2R,3S)-3-(benzyloxy)-1-(trityloxy)pent-4-en-2-yl methanesulfonate

(2S,3S)-2-azido-3-(benzyloxy)-1-(trityloxy)pent-4-ene

tert-butyl (2S,3S)-[3-(benzyloxy)-1-(trityloxy)pent-4-en-2-yl]carbamate

Downstream raw materials:

(3S,4S,5S)-5-(acetoxy)-3-(benzyloxy)-4-(tert-butoxycarbonylamino)cyclohex-1-ene

(1R,2R,3R,4S,5S)-5-(acetoxy)-3-(benzyloxy)-4-(tert-butoxycarbonylamino)cyclohexane-1,2-diol

(1R,2R,3R,4S,5S)-3-(benzyloxy)-4-(tert-butoxycarbonylamino)cyclohexane-1,2,5-triyl triacetate

(3S,4S,5R)-5-(acetoxy)-3-(benzyloxy)-4-(tert-butoxycarbonylamino)cyclohex-1-ene