(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
• Mol file: 430473-72-6.mol

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

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:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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:

S-phenyl 2-methoxyethanethionate (72867-24-4) + (E)-(2S,3R)-2,3-Bis-benzyloxy-6-methyl-hept-4-enal (430473-71-5) → (E)-(2S,3S,4R,5R)-4,5-Bis-benzyloxy-3-hydroxy-2-methoxy-8-methyl-non-6-enethioic acid S-phenyl ester + (E)-(2R,3R,4R,5R)-4,5-Bis-benzyloxy-3-hydroxy-2-methoxy-8-methyl-non-6-enethioic acid S-phenyl ester (430473-72-6)

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:

benzyl bromide (100-39-0) → (E)-(2R,3R,4R,5R)-4,5-Bis-benzyloxy-3-hydroxy-2-methoxy-8-methyl-non-6-enethioic acid S-phenyl ester (430473-72-6)

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:

(2R,3R)-(-)-2,3-bis(phenylmethoxy)-1,4-butanediol (113350-84-8) → (E)-(2R,3R,4R,5R)-4,5-Bis-benzyloxy-3-hydroxy-2-methoxy-8-methyl-non-6-enethioic acid S-phenyl ester (430473-72-6)

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

upstream raw materials:

S-phenyl 2-methoxyethanethionate

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

benzyl bromide

(2R,3R)-(-)-2,3-bis(phenylmethoxy)-1,4-butanediol

Downstream raw materials:

(E)-(2R,3R,4R,5R)-4,5-Bis-benzyloxy-3-hydroxy-2-methoxy-8-methyl-non-6-enoic acid ((S)-2-oxo-azepan-3-yl)-amide