D-ERYTHRURONOLACTONE ACETONIDE

Base Information

• Chemical Name: D-ERYTHRURONOLACTONE ACETONIDE
• CAS No.: 85254-46-2
• Molecular Formula: C₇H₁₀O₅
• Molecular Weight: 174.153
• Mol file: 85254-46-2.mol

Synonyms:D-ERYTHRURONOLACTONE ACETONIDE

Chemical Property of D-ERYTHRURONOLACTONE ACETONIDE

Chemical Property:

• PSA: 64.99000
• LogP: -0.61830

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of D-ERYTHRURONOLACTONE ACETONIDE

There total 2 articles about D-ERYTHRURONOLACTONE ACETONIDE 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: 63.0%

(1R,2S,3S,4R,5S,6S)-1-Chloro-3,4-dihydroxy-5,6-di-O-isopropylidene-1,2-epoxycyclohexane (148132-86-9) → 2,3-(isopropylidenedioxy)-4,4-dihydroxybutanic acid lactone (85254-46-2,126575-56-2)

Guidance literature:

With sodium periodate; water; for 4h; Ambient temperature;

DOI:10.1135/cccc19932517

Reference yield:

(3aS,7aS)-4-chloro-2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole (127666-06-2) → 2,3-(isopropylidenedioxy)-4,4-dihydroxybutanic acid lactone (85254-46-2,126575-56-2)

Guidance literature:

With dimethylsulfide; ozone; Yield given. Multistep reaction; 1.) ethyl acetate, -78 deg C; 2.) 0 deg C, 12 h;

DOI:10.1021/jo00302a037

Reference yield:

2,3-(isopropylidenedioxy)-4,4-dihydroxybutanic acid lactone (85254-46-2,126575-56-2) → (4S,5R)-2,2-dimethyl-4-(2-methylpropan-1-yl)-5-<(1S)-1--2-cyclohexylethyl>-1,3-dioxolane (143285-53-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) n-butyllithium / 1.) THF, hexane, -40 deg C, 1.5 h, 2.) THF, reflux, 1 h

2: diethyl ether / 0 - 5 °C

3: 54 percent / LiAlH₄ / tetrahydrofuran / 2.5 h / 0 - 5 °C

4: 90 percent / H₂ / 10 percent Pd/C / methanol / 24 h / 760 Torr / Ambient temperature

6: 1.) t-BuLi / 1.) pentane, diethyl ether, -80 to -90 deg C, 5 min, 2.) ether, r.t., 1 h

7: 64 percent / H₂ / Raney nickel / methanol / 24 h / 3040 Torr / Ambient temperature

8: CH₂Cl₂ / 18 h / Ambient temperature

With lithium aluminium tetrahydride; n-butyllithium; hydrogen; tert.-butyl lithium; palladium on activated charcoal; nickel; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1021/jo00064a013

upstream raw materials:

(3aS,7aS)-4-chloro-2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole

(1R,2S,3S,4R,5S,6S)-1-Chloro-3,4-dihydroxy-5,6-di-O-isopropylidene-1,2-epoxycyclohexane

Downstream raw materials:

(S)-2-Cyclohexyl-1-((4R,5S)-5-isobutyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethylamine

N'-[(S)-2-Cyclohexyl-1-((4R,5S)-5-isobutyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-N,N-dimethyl-hydrazine

(4S,5R)-2,2-dimethyl-4-(2-methylpropan-1-yl)-5-<(1S)-1--2-cyclohexylethyl>-1,3-dioxolane

(S)-1-((4R,5S)-5-Isobutyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-phenyl-ethylamine

Refernces

• 1、 Hudlicky,Natchus,Nugent. "Improved practical synthesis of a prostaglandin and carbocyclic nucleoside synthon". . p. 151 - 157. Retrieved 2007/10/02.
• 2、 Hudlicky, Tomas,Luna, Hector,Price, John D.,Rulin, Fan. "AN ENANTIODIVERGENT APPROACH TO D- AND L-ERYTHROSE VIA MICROBIAL OXIDATION OF CHLOROBENZENE". . p. 4053 - 4054. Retrieved 2007/10/02.