(E)-(2R,3R,4R,5R)-4,5-Bis-benzyloxy-3-hydroxy-2-methoxy-8-methyl-non-6-enethioic acid S-phenyl ester

Base Information

Chemical Name:(E)-(2R,3R,4R,5R)-4,5-Bis-benzyloxy-3-hydroxy-2-methoxy-8-methyl-non-6-enethioic acid S-phenyl ester
CAS No.:430473-72-6
Molecular Formula:C₃₁H₃₆O₅S
Molecular Weight:520.69
Hs Code.:

Synonyms:(E)-(2R,3R,4R,5R)-4,5-Bis-benzyloxy-3-hydroxy-2-methoxy-8-methyl-non-6-enethioic acid S-phenyl ester

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Chemical Property of (E)-(2R,3R,4R,5R)-4,5-Bis-benzyloxy-3-hydroxy-2-methoxy-8-methyl-non-6-enethioic acid S-phenyl ester

Chemical Property:

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Technology Process of (E)-(2R,3R,4R,5R)-4,5-Bis-benzyloxy-3-hydroxy-2-methoxy-8-methyl-non-6-enethioic acid S-phenyl ester

There total 8 articles about (E)-(2R,3R,4R,5R)-4,5-Bis-benzyloxy-3-hydroxy-2-methoxy-8-methyl-non-6-enethioic acid S-phenyl 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:

: 72867-24-4
S-phenyl 2-methoxyethanethionate

: 430473-71-5
(E)-(2S,3R)-2,3-Bis-benzyloxy-6-methyl-hept-4-enal

: (E)-(2S,3S,4R,5R)-4,5-Bis-benzyloxy-3-hydroxy-2-methoxy-8-methyl-non-6-enethioic acid S-phenyl ester

: 430473-72-6
(E)-(2R,3R,4R,5R)-4,5-Bis-benzyloxy-3-hydroxy-2-methoxy-8-methyl-non-6-enethioic acid S-phenyl ester

Guidance literature:: With N,N-dimethyl-ethanamine; titanium tetrachloride; lithium iodide; In dichloromethane; at -78 ℃;
DOI:10.1016/S0040-4039(02)00022-9

Reference yield:

: 100-39-0
benzyl bromide

: 430473-72-6
(E)-(2R,3R,4R,5R)-4,5-Bis-benzyloxy-3-hydroxy-2-methoxy-8-methyl-non-6-enethioic acid S-phenyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 60 percent / NaH; nBu₄NI / tetrahydrofuran / 20 °C

2: 86 percent / LAH / tetrahydrofuran / 20 °C

3: 92 percent / NaH; nBu₄NI / tetrahydrofuran

4: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

5: LHMDS / tetrahydrofuran / 1 h / -78 - 20 °C

6: 83 percent / TBAF / tetrahydrofuran / 0 °C

7: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

8: EtNMe₂; LiI; TiCl₄ / CH₂Cl₂ / -78 °C

With lithium aluminium tetrahydride; oxalyl dichloride; N,N-dimethyl-ethanamine; tetrabutyl ammonium fluoride; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; lithium iodide; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; 5: Julia olefination;
DOI:10.1016/S0040-4039(02)00022-9

Reference yield:

: 113350-84-8
(2R,3R)-(-)-2,3-bis(phenylmethoxy)-1,4-butanediol

: 430473-72-6
(E)-(2R,3R,4R,5R)-4,5-Bis-benzyloxy-3-hydroxy-2-methoxy-8-methyl-non-6-enethioic acid S-phenyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 92 percent / NaH; nBu₄NI / tetrahydrofuran

2: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

3: LHMDS / tetrahydrofuran / 1 h / -78 - 20 °C

4: 83 percent / TBAF / tetrahydrofuran / 0 °C

5: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

6: EtNMe₂; LiI; TiCl₄ / CH₂Cl₂ / -78 °C

With oxalyl dichloride; N,N-dimethyl-ethanamine; tetrabutyl ammonium fluoride; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; lithium iodide; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; 3: Julia olefination;
DOI:10.1016/S0040-4039(02)00022-9