diethyl 5(S),8(S)-bis(benzoyloxy)-6(R),7(R)-dihydroxy-6,7-O-(1-methylethylidene)-dodecanedioate

Base Information

• Chemical Name: diethyl 5(S),8(S)-bis(benzoyloxy)-6(R),7(R)-dihydroxy-6,7-O-(1-methylethylidene)-dodecanedioate
• CAS No.: 109458-67-5
• Molecular Formula: C₃₃H₄₂O₁₀
• Molecular Weight: 598.69
• Mol file: 109458-67-5.mol

Synonyms:diethyl 5(S),8(S)-bis(benzoyloxy)-6(R),7(R)-dihydroxy-6,7-O-(1-methylethylidene)-dodecanedioate

Chemical Property of diethyl 5(S),8(S)-bis(benzoyloxy)-6(R),7(R)-dihydroxy-6,7-O-(1-methylethylidene)-dodecanedioate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of diethyl 5(S),8(S)-bis(benzoyloxy)-6(R),7(R)-dihydroxy-6,7-O-(1-methylethylidene)-dodecanedioate

There total 7 articles about diethyl 5(S),8(S)-bis(benzoyloxy)-6(R),7(R)-dihydroxy-6,7-O-(1-methylethylidene)-dodecanedioate 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: 100.0%

diethyl 5(S),8(S)-bis(benzoyloxy)-6(R),7(R)-dihydroxy-6,7-O-(1-methylethylidene)-2,10-dodecadiynedioate (119392-29-9) → diethyl 5(S),8(S)-bis(benzoyloxy)-6(R),7(R)-dihydroxy-6,7-O-(1-methylethylidene)-dodecanedioate (109458-67-5)

Guidance literature:

With hydrogen; platinum; In ethanol;

DOI:10.1016/S0040-4039(00)84936-9

Reference yield:

diethyl 5(S),6(R),7(R),8(S)-tetrahydroxy-6,7-O-(1-methylethylidene)-2,10-dodecadiynedioate (119392-28-8) → diethyl 5(S),8(S)-bis(benzoyloxy)-6(R),7(R)-dihydroxy-6,7-O-(1-methylethylidene)-dodecanedioate (109458-67-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / pyridine / 1.) 0 deg C, 0.5 h, 2.) 20 deg C, 2 h

2: 100 percent / PtO₂, hydrogen / ethanol / Ambient temperature

With pyridine; platinum(IV) oxide; hydrogen; In ethanol;

DOI:10.1021/jo00271a032

Reference yield:

1,2:5,6-dianhydro-3,4-O-methylethylidene-L-iditol (63699-97-8) → diethyl 5(S),8(S)-bis(benzoyloxy)-6(R),7(R)-dihydroxy-6,7-O-(1-methylethylidene)-dodecanedioate (109458-67-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) n-BuLi, 2.) boron trifluoride etherate / 1.) THF, -78 deg C, 1 h, 2.) THF, -78 deg C, 2 h

2: 80 percent / pyridine / 1.) 0 deg C, 0.5 h, 2.) 20 deg C, 2 h

3: 100 percent / PtO₂, hydrogen / ethanol / Ambient temperature

With pyridine; platinum(IV) oxide; n-butyllithium; boron trifluoride diethyl etherate; hydrogen; In ethanol;

DOI:10.1021/jo00271a032

upstream raw materials:

diethyl 5(S),8(S)-bis(benzoyloxy)-6(R),7(R)-dihydroxy-6,7-O-(1-methylethylidene)-2,10-dodecadiynedioate

diethyl 5(S),6(R),7(R),8(S)-tetrahydroxy-6,7-O-(1-methylethylidene)-2,10-dodecadiynedioate

benzoyl chloride

1,2:5,6-dianhydro-3,4-O-methylethylidene-L-iditol

Downstream raw materials:

diethyl 5(S),8(S)-bis(benzoyloxy)-6(S),7(S)-dihydroxydodecanedioate

6-trans-Leukotriene B₄

(5S,12R,6Z,8E,10E,14Z)-ethyl 5-benzoyloxy-12-hydroxyicosatetra-6,8,10,14-enoate

ethyl 5(S)-(benzoyloxy)-12(R)-<(tert-butyldiphenylsilyl)oxy>-6(E),8(E),10(E),14(Z)-icosatetraenoate