L-lyxo-Hepturonic acid, 2,5-anhydro-3,6-dideoxy-2,4-di-C-ethyl-, gamma-lactone (9CI)

Base Information

• Chemical Name: L-lyxo-Hepturonic acid, 2,5-anhydro-3,6-dideoxy-2,4-di-C-ethyl-, gamma-lactone (9CI)
• CAS No.: 460076-98-6
• Molecular Formula: C11H16O4
• Molecular Weight: 212.24234
• Mol file: 460076-98-6.mol

Synonyms:L-lyxo-Hepturonic acid, 2,5-anhydro-3,6-dideoxy-2,4-di-C-ethyl-, gamma-lactone (9CI)

Chemical Property of L-lyxo-Hepturonic acid, 2,5-anhydro-3,6-dideoxy-2,4-di-C-ethyl-, gamma-lactone (9CI)

Chemical Property:

• PSA: 52.60000
• LogP: 1.21870

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of L-lyxo-Hepturonic acid, 2,5-anhydro-3,6-dideoxy-2,4-di-C-ethyl-, gamma-lactone (9CI)

There total 11 articles about L-lyxo-Hepturonic acid, 2,5-anhydro-3,6-dideoxy-2,4-di-C-ethyl-, gamma-lactone (9CI) 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:

(3aS,5R,6aS)-5,6a-diethyl-5-(hydroxymethyl)tetrahydrofuro[3,2-b]furan-2(5H)-one (460076-87-3) → (2R,3aS,6aS)-2,3a-Diethyl-5-oxo-hexahydro-furo[3,2-b]furan-2-carbaldehyde (460076-98-6,477772-09-1)

Guidance literature:

With Chloro-oxo-acetic acid; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 1h;

DOI:10.1021/ja026728s

Reference yield:

(3R)-3-hydroxy-3-(hydroxymethyl)-3,3'-O-isopropylidenepentanal (106268-09-1) → (2R,3aS,6aS)-2,3a-Diethyl-5-oxo-hexahydro-furo[3,2-b]furan-2-carbaldehyde (460076-98-6,477772-09-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: TPAP; NMO

2.1: 61 percent / Dowex 50; MeOH

3.1: CuCl₂; NaOAc; AcOH / PdCl₂

3.2: K₂CO₃ / methanol

4.1: oxalylchloride; DMSO / CH₂Cl₂ / 1 h / -78 °C

With methanol; N-methyl-2-indolinone; tetrapropylammonium perruthennate; Chloro-oxo-acetic acid; Dowex 50; sodium acetate; acetic acid; dimethyl sulfoxide; copper dichloride; palladium dichloride; In dichloromethane;

DOI:10.1021/ja026728s

Reference yield:

(R)-2-(4-ethyl-2,2-dimethyl-1,3-dioxolan-4-yl)ethanol (460076-90-8) → (2R,3aS,6aS)-2,3a-Diethyl-5-oxo-hexahydro-furo[3,2-b]furan-2-carbaldehyde (460076-98-6,477772-09-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: TPAP; NMO

2.1: TPAP; NMO

3.1: 61 percent / Dowex 50; MeOH

4.1: CuCl₂; NaOAc; AcOH / PdCl₂

4.2: K₂CO₃ / methanol

5.1: oxalylchloride; DMSO / CH₂Cl₂ / 1 h / -78 °C

With methanol; N-methyl-2-indolinone; tetrapropylammonium perruthennate; Chloro-oxo-acetic acid; Dowex 50; sodium acetate; acetic acid; dimethyl sulfoxide; copper dichloride; palladium dichloride; In dichloromethane;

DOI:10.1021/ja026728s

upstream raw materials:

(3aS,5R,6aS)-5,6a-diethyl-5-(hydroxymethyl)tetrahydrofuro[3,2-b]furan-2(5H)-one

(3R)-3-hydroxy-3-(hydroxymethyl)-3,3'-O-isopropylidenepentanal

(R)-2-(4-ethyl-2,2-dimethyl-1,3-dioxolan-4-yl)ethanol

(4R)-1-(4-ethyl-2,2-dimethyl-1,3-dioxolan-4-yl)butan-2-ol

Refernces

• 1、 Xie, Xin-Gang,Wu, Xun-Wei,Lee, Hing-Ken,Peng, Xiao-Shui,Wong, Henry N. C.. "Total synthesis of plakortone B". supporting information; experimental part. p. 6933 - 6941. Retrieved 2010/08/22.