(+)-(4S-cis)-2,2-dimethyl-5-<(benzoyloxy)methyl>-1,3-dioxolane-4-butanoic acid 3-hydroxypropyl ester

Base Information

• Chemical Name: (+)-(4S-cis)-2,2-dimethyl-5-<(benzoyloxy)methyl>-1,3-dioxolane-4-butanoic acid 3-hydroxypropyl ester
• CAS No.: 77333-01-8
• Molecular Formula: C₂₀H₂₈O₇
• Molecular Weight: 380.438
• Mol file: 77333-01-8.mol

Synonyms:(+)-(4S-cis)-2,2-dimethyl-5-<(benzoyloxy)methyl>-1,3-dioxolane-4-butanoic acid 3-hydroxypropyl ester

Chemical Property of (+)-(4S-cis)-2,2-dimethyl-5-<(benzoyloxy)methyl>-1,3-dioxolane-4-butanoic acid 3-hydroxypropyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(4S-cis)-2,2-dimethyl-5-<(benzoyloxy)methyl>-1,3-dioxolane-4-butanoic acid 3-hydroxypropyl ester

There total 16 articles about (+)-(4S-cis)-2,2-dimethyl-5-<(benzoyloxy)methyl>-1,3-dioxolane-4-butanoic acid 3-hydroxypropyl ester 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: 60.3%

(-)-(4S-trans)-2,2-dimethyl-5-<3-(1,3-dioxan-2-yl)propyl>-1,3-dioxolane-4-methanol benzoate (77333-00-7,85648-04-0) → (-)-(4S-trans)-5-<(benzoyloxy)methyl>-2,2-dimethyl-1,3-dioxolane-4-butanoic acid 3-hydroxypropyl ester (77333-01-8)

Guidance literature:

With oxygen; ozone; In ethyl acetate; at -70 ℃; for 3h;

DOI:10.1021/ja00349a053

Reference yield:

[(4R,5S)-5-((Z)-3-[1,3]Dioxan-2-yl-propenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methanol (85612-85-7) → (+)-(4S-cis)-2,2-dimethyl-5-<(benzoyloxy)methyl>-1,3-dioxolane-4-butanoic acid 3-hydroxypropyl ester (77333-01-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 40.8 g / pyridine / 3 h / 5 °C

2: 100 percent / hydrogen / platinum oxide / ethyl acetate / 6 h / Ambient temperature

3: 69.4 percent / ozone, oxygen / ethyl acetate / 5 h / -70 °C

With pyridine; hydrogen; oxygen; ozone; platinum(IV) oxide; In ethyl acetate;

DOI:10.1021/ja00349a053

Reference yield:

2-(1,3-dioxan-2-yl)ethyltriphenylphosphonium bromide (69891-92-5) → (-)-(4S-trans)-5-<(benzoyloxy)methyl>-2,2-dimethyl-1,3-dioxolane-4-butanoic acid 3-hydroxypropyl ester (77333-01-8)

Guidance literature:

Multi-step reaction with 4 steps

1: n-butyllithium / tetrahydrofuran / 0.33 h / -25 °C

2: 46.9 percent / tetrahydrofuran / 1) -25 deg C, 30 min; 2) room temperature, 1.5 h

3: 98.2 percent / hydrogen / platinum oxide / ethyl acetate / 6 h / Ambient temperature

4: 60.3 percent / ozone, oxygen / ethyl acetate / 3 h / -70 °C

With n-butyllithium; hydrogen; oxygen; ozone; platinum(IV) oxide; In tetrahydrofuran; ethyl acetate;

DOI:10.1021/ja00349a053

upstream raw materials:

D-erythronolactone acetonide

4,6-O-isopropylidene-D-glucopyranose

dioxanylethyl phosphorane

2-(1,3-dioxan-2-yl)ethyltriphenylphosphonium bromide

Downstream raw materials:

(+)--6-<2-<(benzoyloxy)-1-hydroxy>ethyl>tetrahydro-2H-pyran-2-one

Benzoic acid (S)-2-methanesulfonyloxy-2-((S)-6-oxo-tetrahydro-pyran-2-yl)-ethyl ester

Benzoic acid (R)-2-methanesulfonyloxy-2-((S)-6-oxo-tetrahydro-pyran-2-yl)-ethyl ester

(5S,6S)-epoxy-10-formyl-(7E,9E)-decadienoic acid methyl ester

Refernces

• 1、 Cohen, Noal,Banner, Bruce L.,Lopresti, Rocco J.. "Synthesis of optically active leukotriene (SRS-A) intermediates". . p. 4163 - 4166. Retrieved 2007/10/02.