(Z)-(2S,3R,6S,8R)-8-(9H-Fluoren-9-ylmethoxycarbonylamino)-3,6-dihydroxy-2,10-dimethyl-undec-4-enethioic acid S-benzyl ester

Base Information

Chemical Name:(Z)-(2S,3R,6S,8R)-8-(9H-Fluoren-9-ylmethoxycarbonylamino)-3,6-dihydroxy-2,10-dimethyl-undec-4-enethioic acid S-benzyl ester
CAS No.:504412-86-6
Molecular Formula:C₃₅H₄₁NO₅S
Molecular Weight:587.78
Hs Code.:

Synonyms:(Z)-(2S,3R,6S,8R)-8-(9H-Fluoren-9-ylmethoxycarbonylamino)-3,6-dihydroxy-2,10-dimethyl-undec-4-enethioic acid S-benzyl ester

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Chemical Property of (Z)-(2S,3R,6S,8R)-8-(9H-Fluoren-9-ylmethoxycarbonylamino)-3,6-dihydroxy-2,10-dimethyl-undec-4-enethioic acid S-benzyl ester

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Technology Process of (Z)-(2S,3R,6S,8R)-8-(9H-Fluoren-9-ylmethoxycarbonylamino)-3,6-dihydroxy-2,10-dimethyl-undec-4-enethioic acid S-benzyl ester

There total 12 articles about (Z)-(2S,3R,6S,8R)-8-(9H-Fluoren-9-ylmethoxycarbonylamino)-3,6-dihydroxy-2,10-dimethyl-undec-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: 84.0%

: 504412-16-2
(S)-2-{(4R,7S)-7-[(R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-methyl-pentyl]-2,2-dimethyl-4,7-dihydro-[1,3,2]dioxasilepin-4-yl}-thiopropionic acid S-benzyl ester

: 504412-86-6
(Z)-(2S,3R,6S,8R)-8-(9H-Fluoren-9-ylmethoxycarbonylamino)-3,6-dihydroxy-2,10-dimethyl-undec-4-enethioic acid S-benzyl ester

Guidance literature:: With pyridine; hydrogen fluoride; In tetrahydrofuran; at 20 ℃; for 3h;
DOI:10.1021/ol027116f

Reference yield:

: 3-({1-[2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-methyl-pentyl]-allyloxy}-dimethyl-silanyloxy)-2-methyl-pent-4-enethioic acid S-benzyl ester

: 504412-86-6
(Z)-(2S,3R,6S,8R)-8-(9H-Fluoren-9-ylmethoxycarbonylamino)-3,6-dihydroxy-2,10-dimethyl-undec-4-enethioic acid S-benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 75 percent / Cl₂(PCy₃)(IMesH₂)Ru=CHPh / toluene / 3 h / 75 °C

2: 84 percent / HF; pyridine / tetrahydrofuran / 3 h / 20 °C

With pyridine; hydrogen fluoride; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; toluene;
DOI:10.1021/ol027116f

Reference yield:

: 16937-99-8,53296-34-7
N-Boc-D-Leu

: 504412-86-6
(Z)-(2S,3R,6S,8R)-8-(9H-Fluoren-9-ylmethoxycarbonylamino)-3,6-dihydroxy-2,10-dimethyl-undec-4-enethioic acid S-benzyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: N-methylmorpholine; ClCO₂-i-Bu / tetrahydrofuran / 0.33 h / -20 °C

1.2: 81 percent / tetrahydrofuran; diethyl ether / 0.5 h / -20 °C

2.1: 100 percent / PhCO₂Ag; Et₃N / 1.25 h

3.1: 80 percent / DIBAL-H / toluene / 1 h / -78 °C

4.1: 47 percent / tetrahydrofuran / 1.5 h / -70 - -40 °C

5.1: aq.HCl / dioxane / 1 h

6.1: DIPEA / CH₂Cl₂ / 0.25 h

7.1: 74 percent / pyridine / 3 h

8.1: 75 percent / Cl₂(PCy₃)(IMesH₂)Ru=CHPh / toluene / 3 h / 75 °C

9.1: 84 percent / HF; pyridine / tetrahydrofuran / 3 h / 20 °C

With 4-methyl-morpholine; pyridine; hydrogenchloride; hydrogen fluoride; silver benzoate; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; isobutyl chloroformate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; 1,4-dioxane; dichloromethane; toluene; 2.1: Wolff rearrangement;
DOI:10.1021/ol027116f