2,3-dideoxy-D-arabino-hept-2-enoic acid δ-lactone 4,6-diacetate 7-benzoate

Base Information

• Chemical Name: 2,3-dideoxy-D-arabino-hept-2-enoic acid δ-lactone 4,6-diacetate 7-benzoate
• CAS No.: 1003600-48-3
• Molecular Formula: C₁₈H₁₈O₈
• Molecular Weight: 362.336
• Mol file: 1003600-48-3.mol

Synonyms:2,3-dideoxy-D-arabino-hept-2-enoic acid δ-lactone 4,6-diacetate 7-benzoate

Chemical Property of 2,3-dideoxy-D-arabino-hept-2-enoic acid δ-lactone 4,6-diacetate 7-benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3-dideoxy-D-arabino-hept-2-enoic acid δ-lactone 4,6-diacetate 7-benzoate

There total 92 articles about 2,3-dideoxy-D-arabino-hept-2-enoic acid δ-lactone 4,6-diacetate 7-benzoate 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: 96.0%

Acetyl bromide (506-96-7) + 7-O-benzoyl-4,6-di-O-benzyl-2,3-dideoxy-D-arabinohept-2-eno-1,5-lactone → 2,3-dideoxy-D-arabino-hept-2-enoic acid δ-lactone 4,6-diacetate 7-benzoate (1003600-48-3)

Guidance literature:

4,6,7-tri-O-benzyl-2,3-dideoxy-D-arabinohept-2-eno-1,5-lactone; With iron(III) chloride; benzoic acid anhydride; benzoic acid; In dichloromethane; at 20 ℃; for 24h;

Acetyl bromide; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1016/j.ejmech.2020.112597

Reference yield: 95.0%

(R)-2-acetoxy-2-((2S,3R)-3-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl benzoate (1308247-32-6) + acetic anhydride (108-24-7) → 2,3-dideoxy-D-arabino-hept-2-enoic acid δ-lactone 4,6-diacetate 7-benzoate (1003600-48-3)

Guidance literature:

With toluene-4-sulfonic acid; at 20 ℃; for 4h;

DOI:10.1016/j.bioorg.2020.104491

Reference yield: 88.0%

(R)-2-(benzyloxy)-2-((2R,3R)-3-((tert-butyldimethylsilyl)oxy)-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl benzoate + acetic anhydride (108-24-7) → 2,3-dideoxy-D-arabino-hept-2-enoic acid δ-lactone 4,6-diacetate 7-benzoate (1003600-48-3)

Guidance literature:

With iron(III) chloride; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1016/j.tet.2018.10.063

upstream raw materials:

C₁₄H₁₄O₆

acetic anhydride

C₁₇H₂₆O₆

C₁₇H₂₄O₆

Refernces

Stereoselective total synthesis of (-)-cleistenolide

10.1016/j.tet.2011.03.107

The research describes the development of a stereoselective total synthesis route for the natural product (?)-cleistenolide, derived from D-(?)-isoascorbic acid. The purpose of this study is to develop a new synthetic strategy for (?)-cleistenolide, a compound with significant biomedical importance due to its antibacterial and antifungal activities. The key steps in this synthesis include highly diastereoselective reduction, one-pot protection of required benzoyl and acetyl groups, and a ring-closing metathesis (RCM) reaction using the Grubbs catalyst. The synthesis starts from D-(?)-isoascorbic acid, which is converted into various intermediates through a series of reactions involving reagents such as TBDMSCl for protection, DIBAL-H for reduction, and K-Selectride for selective diastereomeric reduction. The RCM reaction using the Grubbs second generation catalyst is crucial for forming the desired ring structure. The final product, (?)-cleistenolide, is obtained with an overall yield of 18% and its physical and spectroscopic data match those of the natural product. The study concludes that the developed synthetic route is highly diastereoselective and efficient, providing a valuable method for the synthesis of (?)-cleistenolide and potentially other related bioactive compounds.