(1S,2S,8S,8aR,5'R,2''S)-(R)-1-phenylethyl 1,2,6,7,8,8a-hexahydro-5'-hydroxy-2-methyl-8-<(2-methyl-1-oxobutyl)oxy>-3'-oxo-1-naphthalenehept-1'-enoate

Base Information

Chemical Name:(1S,2S,8S,8aR,5'R,2''S)-(R)-1-phenylethyl 1,2,6,7,8,8a-hexahydro-5'-hydroxy-2-methyl-8-<(2-methyl-1-oxobutyl)oxy>-3'-oxo-1-naphthalenehept-1'-enoate
CAS No.:109721-03-1
Molecular Formula:C₃₁H₄₀O₆
Molecular Weight:508.655
Hs Code.:

Synonyms:(1S,2S,8S,8aR,5'R,2''S)-(R)-1-phenylethyl 1,2,6,7,8,8a-hexahydro-5'-hydroxy-2-methyl-8-<(2-methyl-1-oxobutyl)oxy>-3'-oxo-1-naphthalenehept-1'-enoate

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Chemical Property of (1S,2S,8S,8aR,5'R,2''S)-(R)-1-phenylethyl 1,2,6,7,8,8a-hexahydro-5'-hydroxy-2-methyl-8-<(2-methyl-1-oxobutyl)oxy>-3'-oxo-1-naphthalenehept-1'-enoate

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Technology Process of (1S,2S,8S,8aR,5'R,2''S)-(R)-1-phenylethyl 1,2,6,7,8,8a-hexahydro-5'-hydroxy-2-methyl-8-<(2-methyl-1-oxobutyl)oxy>-3'-oxo-1-naphthalenehept-1'-enoate

There total 5 articles about (1S,2S,8S,8aR,5'R,2''S)-(R)-1-phenylethyl 1,2,6,7,8,8a-hexahydro-5'-hydroxy-2-methyl-8-<(2-methyl-1-oxobutyl)oxy>-3'-oxo-1-naphthalenehept-1'-enoate 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: 42.0%

: 96575-19-8
(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-formyl-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

: 96555-53-2
(R)-dimethyl <<4-<<(R)-phenylethoxy>carbonyl>-3-hydroxybutyryl>methyl>phosphonate

: 109721-03-1
(1S,2S,8S,8aR,5'R,2''S)-(R)-1-phenylethyl 1,2,6,7,8,8a-hexahydro-5'-hydroxy-2-methyl-8-<(2-methyl-1-oxobutyl)oxy>-3'-oxo-1-naphthalenehept-1'-enoate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In acetonitrile;
DOI:10.1021/ja00298a062

Reference yield:

: 96575-20-1
(3R,1'R)-methyl 1'-phenylethyl 3-hydroxypentanedioate

: 109721-03-1
(1S,2S,8S,8aR,5'R,2''S)-(R)-1-phenylethyl 1,2,6,7,8,8a-hexahydro-5'-hydroxy-2-methyl-8-<(2-methyl-1-oxobutyl)oxy>-3'-oxo-1-naphthalenehept-1'-enoate

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) N-BuLi / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, from -78 deg C to RT

2: 42 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / acetonitrile

With n-butyllithium; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In acetonitrile;
DOI:10.1021/jm00393a030

Reference yield:

: 96555-51-0
(3R,1'R)-methyl 1'-phenylethyl 3-<(tert-butyldimethylsilyl)oxy>pentanedioate

: 109721-03-1
(1S,2S,8S,8aR,5'R,2''S)-(R)-1-phenylethyl 1,2,6,7,8,8a-hexahydro-5'-hydroxy-2-methyl-8-<(2-methyl-1-oxobutyl)oxy>-3'-oxo-1-naphthalenehept-1'-enoate

Guidance literature:: Multi-step reaction with 3 steps

1: 99 percent / aq. HF / acetonitrile / 1.25 h / Ambient temperature

2: 1.) N-BuLi / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, from -78 deg C to RT

3: 42 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / acetonitrile

With n-butyllithium; hydrogen fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In acetonitrile;
DOI:10.1021/jm00393a030