N-Boc-3,4-dehydro-D-proline

Base Information

• Chemical Name: N-Boc-3,4-dehydro-D-proline
• CAS No.: 58617-29-1
• Molecular Formula: C₁₀H₁₅NO₄
• Molecular Weight: 213.233
• Hs Code.: 2933998090
• Mol file: 58617-29-1.mol

Synonyms:N-Boc-3,4-dehydro-D-proline

Chemical Property of N-Boc-3,4-dehydro-D-proline

Chemical Property:

• Boiling Point: 336.4±42.0 °C(Predicted)
• PKA: 3.70±0.20(Predicted)
• PSA: 66.84000
• Density: 1.236±0.06 g/cm3(Predicted)
• LogP: 1.18440

Purity/Quality:

98.5% ^*data from raw suppliers

N-BOC-3,4-DEHYDRO-D-PROLINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-Boc-3,4-dehydro-D-proline

There total 8 articles about N-Boc-3,4-dehydro-D-proline 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: 76.0%

N-tert-Butyloxycarbonyl-3,4-dehydro-DL-prolin (51077-13-5) → N-tert-Butyloxycarbonyl-L-prolin (51077-13-5,51154-06-4,58617-29-1)

Guidance literature:

With (R)-2-methyl-p-nitrobenzylamine;

Reference yield:

(R)-2-Formyl-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester → N-(tert-butoxycarbonyl)-D-3,4-dehydroproline (58617-29-1)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate;

Reference yield:

tert-butyl (2R)-2-(hydroxymethyl)-2,5-dihydro-1H-pyrrole-1-carboxylate (220652-50-6) → N-(tert-butoxycarbonyl)-D-3,4-dehydroproline (58617-29-1)

Guidance literature:

Multi-step reaction with 2 steps

1: Swern oxidation

2: NaClO₂, NaH₂PO₄

With sodium chlorite; sodium dihydrogenphosphate;

upstream raw materials:

N-tert-Butyloxycarbonyl-3,4-dehydro-DL-prolin

tert-butyldicarbonate

DL-3,4-Dehydroproline

tert-butyl (2R)-2-(hydroxymethyl)-2,5-dihydro-1H-pyrrole-1-carboxylate

Downstream raw materials:

N-Tosyl-3,4-dehydro-L-prolin

N-Tosyl-3,4-dehydro-L-prolin-methylester

N-Tosyl-3,4-epoxy-L-prolin-methylester

Refernces

• 1、 Kahl, Jens-Uwe,Wieland, Theodor. "Synthesis of Two Naturally Occuring Diastereomeric Dihydroxyprolines: 2,3-trans-3,4-trans-3,4-Dihydroxy-L-proline and 2,3-cis-3,4-trans-3,4-Dihydroxy-L-proline". . p. 1445 - 1450. Retrieved 2007/10/02.