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

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Chemical Name:diethyl 5(S),8(S)-bis(benzoyloxy)-6(R),7(R)-dihydroxy-6,7-O-(1-methylethylidene)-2,10-dodecadiynedioate
CAS No.:119392-29-9
Molecular Formula:C₃₃H₃₄O₁₀
Molecular Weight:590.627
Hs Code.:

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

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

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

There total 3 articles about diethyl 5(S),8(S)-bis(benzoyloxy)-6(R),7(R)-dihydroxy-6,7-O-(1-methylethylidene)-2,10-dodecadiynedioate 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: 80.0%

: 119392-28-8
diethyl 5(S),6(R),7(R),8(S)-tetrahydroxy-6,7-O-(1-methylethylidene)-2,10-dodecadiynedioate

: 98-88-4
benzoyl chloride

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

Guidance literature:: With pyridine; 1.) 0 deg C, 0.5 h, 2.) 20 deg C, 2 h;
DOI:10.1021/jo00271a032

Reference yield:

: 63699-97-8
1,2:5,6-dianhydro-3,4-O-methylethylidene-L-iditol

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

Guidance literature:: Multi-step reaction with 2 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

With pyridine; n-butyllithium; boron trifluoride diethyl etherate;
DOI:10.1021/jo00271a032

Reference yield:

: 72036-30-7
ethyl 3-lithiopropiolate

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

Guidance literature:: Multi-step reaction with 2 steps

1: BF₃*OEt₂ / tetrahydrofuran / 2 h / -78 °C

2: pyridine / 2 h / 20 °C

With boron trifluoride diethyl etherate; In tetrahydrofuran; pyridine;
DOI:10.1016/S0040-4039(00)84936-9