METHYL-(-)-5S,6S)-EPOXY 7-HYDROXYHEPTANOATE

Base Information

• Chemical Name: METHYL-(-)-5S,6S)-EPOXY 7-HYDROXYHEPTANOATE
• CAS No.: 73957-99-0
• Molecular Formula: C8H14 O4
• Molecular Weight: 174.197
• Mol file: 73957-99-0.mol

Synonyms:Oxiranebutanoicacid, 3-(hydroxymethyl)-, methyl ester, (2S,3S)- (9CI); Oxiranebutanoic acid,3-(hydroxymethyl)-, methyl ester, (2S-trans)-

Chemical Property of METHYL-(-)-5S,6S)-EPOXY 7-HYDROXYHEPTANOATE

Chemical Property:

• PSA: 59.06000
• LogP: 0.08940

Purity/Quality:

97% ^*data from raw suppliers

METHYL-(-)-(5S,6S)-EPOXY-7-HYDROXYHEPTANOATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (2S,3S)-3-(Hydroxymethyl)oxiranebutanoic Acid Methyl Ester was used in total synthesis and determination fo absolute configuration of frondosin B.

Technology Process of METHYL-(-)-5S,6S)-EPOXY 7-HYDROXYHEPTANOATE

There total 64 articles about METHYL-(-)-5S,6S)-EPOXY 7-HYDROXYHEPTANOATE 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: 99.0%

methyl (S,S-trans)-4-(3-benzyloxymethyloxiran-2-yl)butanoate (145799-40-2) → (-)-(S,S-trans)-3-(hydroxymethyl)oxiranebutanoic acid methyl ester (73957-99-0)

Guidance literature:

With hydrogen; palladium dihydroxide; In methanol; chloroform; for 0.333333h; under 760 Torr; Ambient temperature;

Reference yield: 98.0%

C29H30O9S (73957-98-9) → (+/-)-methyl trans-5,6-epoxy-7-hydroxyheptanoate (73957-99-0,77341-36-7,77519-23-4,79356-62-0,79356-66-4,114530-61-9,127760-14-9)

Guidance literature:

With potassium carbonate; In methanol; at 23 ℃; for 2h;

DOI:10.1021/ja00524a045

Reference yield: 96.0%

7-acetoxy-(5S,6S)-epoxyheptanoic acid methyl ester (76871-82-4) → (-)-(S,S-trans)-3-(hydroxymethyl)oxiranebutanoic acid methyl ester (73957-99-0)

Guidance literature:

With methanol; potassium carbonate; sodium sulfate; at 20 ℃;

DOI:10.1016/S0040-4039(99)02201-7

upstream raw materials:

methyl (Z)-7-hydroxy-5-heptenoate

cis-7-hydroxy-5-heptenoic acid,methyl ester

C₂₉H₃₀O₉S

2-(6-hydroxy-4-hexynyl)-1,3-dioxolane

Downstream raw materials:

methyl 10-formyl-5,6E-epoxy-7E,9E-decadienoate

(7E,9E,11Z,14Z)-(5S,6R)-6-[2-(4-Amino-4-carboxy-butyrylamino)-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-5-hydroxy-icosa-7,9,11,14-tetraenoic acid methyl ester

4-[(2S,3S)-3-((1Z,3E)-5-Oxo-penta-1,3-dienyl)-oxiranyl]-butyric acid methyl ester

(7E,9E,11Z,14Z)-6-[2-Amino-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-5-hydroxy-icosa-7,9,11,14-tetraenoic acid methyl ester

Refernces

• 1、 Masayuki, Inoue,Carson, Mattew W.,Frontier, Alison J.,Danishefsky, Samuel J.. "Total Synthesis and Determination of the Absolute Configuration of Frondosin B". . p. 1878 - 1889. Retrieved 2007/10/03.
• 2、 Rodriguez, Ana,Nomen, Miguel,Spur, Bernd W.,Godfroid, Jean-Jacques,Lee, Tak H.. "Total synthesis of leukotrienes from butadiene". . p. 2991 - 3000. Retrieved 2007/10/03.