(2R,3S,6R,7R)-7-(9H-fluoren-9-ylmethoxycarbonylamino)-3,6-dihydroxy-2-isobutyl-9-methyldec-4-enethioic acid S-benzyl ester

Base Information

Chemical Name:(2R,3S,6R,7R)-7-(9H-fluoren-9-ylmethoxycarbonylamino)-3,6-dihydroxy-2-isobutyl-9-methyldec-4-enethioic acid S-benzyl ester
CAS No.:318957-65-2
Molecular Formula:C₃₇H₄₅NO₅S
Molecular Weight:615.834
Hs Code.:

Synonyms:(2R,3S,6R,7R)-7-(9H-fluoren-9-ylmethoxycarbonylamino)-3,6-dihydroxy-2-isobutyl-9-methyldec-4-enethioic acid S-benzyl ester

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Chemical Property of (2R,3S,6R,7R)-7-(9H-fluoren-9-ylmethoxycarbonylamino)-3,6-dihydroxy-2-isobutyl-9-methyldec-4-enethioic acid S-benzyl ester

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Technology Process of (2R,3S,6R,7R)-7-(9H-fluoren-9-ylmethoxycarbonylamino)-3,6-dihydroxy-2-isobutyl-9-methyldec-4-enethioic acid S-benzyl ester

There total 12 articles about (2R,3S,6R,7R)-7-(9H-fluoren-9-ylmethoxycarbonylamino)-3,6-dihydroxy-2-isobutyl-9-methyldec-4-enethioic acid S-benzyl 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:

: 38136-29-7
4-methylvaleroyl chloride

: 318957-65-2
(2R,3S,6R,7R)-7-(9H-fluoren-9-ylmethoxycarbonylamino)-3,6-dihydroxy-2-isobutyl-9-methyldec-4-enethioic acid S-benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C

2.1: Bu₂BOTf; i-Pr₂NEt / CH₂Cl₂ / -78 - 0 °C

3.1: AlMe₃ / CH₂Cl₂; toluene / 0.5 h / 0 °C

4.1: pyridine / 2 h / 20 °C

4.2: pyridine / 1.5 h / 20 °C

5.1: 70 percent / Cl₂(IMes)(PCy₃)Ru=CHPh / toluene / 1 h / 75 °C

6.1: HF / pyridine; tetrahydrofuran / 0.5 h / 20 °C

With n-butyllithium; di-n-butylboryl trifluoromethanesulfonate; hydrogen fluoride; trimethylaluminum; N-ethyl-N,N-diisopropylamine; Cl₂(PCy₃)(N,N'-(Mes)2-imidazolidin-2-yl)Ru=CHC₆H₅; In tetrahydrofuran; pyridine; hexane; dichloromethane; toluene; 1.1: Addition / 2.1: Addition / 3.1: Substitution / 4.1: silylation / 4.2: silylation / 5.1: Cyclization / 6.1: Ring cleavage;
DOI:10.1021/ol006560k

Reference yield:

: (R)-2-{(4S,7R)-7-[(R)-1-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-methyl-butyl]-2,2-dimethyl-4,7-dihydro-[1,3,2]dioxasilepin-4-yl}-4-methyl-pentanethioic acid S-benzyl ester

: 318957-65-2
(2R,3S,6R,7R)-7-(9H-fluoren-9-ylmethoxycarbonylamino)-3,6-dihydroxy-2-isobutyl-9-methyldec-4-enethioic acid S-benzyl ester

Guidance literature:: With hydrogen fluoride; In tetrahydrofuran; pyridine; at 20 ℃; for 0.5h;
DOI:10.1021/ol006560k

Reference yield:

: 227293-93-8
(4R,5S)-3-((2R,3S)-3-Hydroxy-2-isobutyl-pent-4-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one

: 318957-65-2
(2R,3S,6R,7R)-7-(9H-fluoren-9-ylmethoxycarbonylamino)-3,6-dihydroxy-2-isobutyl-9-methyldec-4-enethioic acid S-benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: AlMe₃ / CH₂Cl₂; toluene / 0.5 h / 0 °C

2.1: pyridine / 2 h / 20 °C

2.2: pyridine / 1.5 h / 20 °C

3.1: 70 percent / Cl₂(IMes)(PCy₃)Ru=CHPh / toluene / 1 h / 75 °C

4.1: HF / pyridine; tetrahydrofuran / 0.5 h / 20 °C

With hydrogen fluoride; trimethylaluminum; Cl₂(PCy₃)(N,N'-(Mes)2-imidazolidin-2-yl)Ru=CHC₆H₅; In tetrahydrofuran; pyridine; dichloromethane; toluene; 1.1: Substitution / 2.1: silylation / 2.2: silylation / 3.1: Cyclization / 4.1: Ring cleavage;
DOI:10.1021/ol006560k