(3aR,4R,5S,7R,7aR)-3a-Hydroxy-7-methoxy-5-phenylsulfanyl-octahydro-benzofuran-4-carboxylic acid methyl ester

Base Information

• Chemical Name: (3aR,4R,5S,7R,7aR)-3a-Hydroxy-7-methoxy-5-phenylsulfanyl-octahydro-benzofuran-4-carboxylic acid methyl ester
• CAS No.: 113643-25-7
• Molecular Formula: C₁₇H₂₂O₅S
• Molecular Weight: 338.425
• Mol file: 113643-25-7.mol

Synonyms:(3aR,4R,5S,7R,7aR)-3a-Hydroxy-7-methoxy-5-phenylsulfanyl-octahydro-benzofuran-4-carboxylic acid methyl ester

Chemical Property of (3aR,4R,5S,7R,7aR)-3a-Hydroxy-7-methoxy-5-phenylsulfanyl-octahydro-benzofuran-4-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,4R,5S,7R,7aR)-3a-Hydroxy-7-methoxy-5-phenylsulfanyl-octahydro-benzofuran-4-carboxylic acid methyl ester

There total 6 articles about (3aR,4R,5S,7R,7aR)-3a-Hydroxy-7-methoxy-5-phenylsulfanyl-octahydro-benzofuran-4-carboxylic acid methyl 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: 89.0%

lithium thiophenoxide (2973-86-6) + (E)-(R)-5-Methoxy-5-((R)-3-oxo-tetrahydro-furan-2-yl)-pent-2-enoic acid methyl ester (113643-24-6) → (3aR,4R,5S,7R,7aR)-3a-Hydroxy-7-methoxy-5-phenylsulfanyl-octahydro-benzofuran-4-carboxylic acid methyl ester (113643-25-7)

Guidance literature:

With trimethylaluminum; In tetrahydrofuran; at 0 ℃;

DOI:10.1016/S0040-4039(00)96669-3

Reference yield:

(3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde (33985-40-9) → (3aR,4R,5S,7R,7aR)-3a-Hydroxy-7-methoxy-5-phenylsulfanyl-octahydro-benzofuran-4-carboxylic acid methyl ester (113643-25-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 1) BF₃OEt₂; 2) NaH / 1) CH₂Cl₂; 2) THF

2: 1) HCl; 2) BF₃OEt₂, Et₃SiH / 1) MeOH; 2) CH₂Cl₂

3: 1) (CH₃)2C(OAc)COBr; 2) Amberlite IRA-400 / 2) MeOH

4: 91 percent / LiEt₃BH / tetrahydrofuran

6: 89 percent / trimethylaluminum / tetrahydrofuran / 0 °C

With hydrogenchloride; triethylsilane; Amberlite IRA-400; boron trifluoride diethyl etherate; acetoxyisobutyryl bromide; trimethylaluminum; sodium hydride; lithium triethylborohydride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)96669-3

Reference yield:

(2S,3S)-2-((R)-1-Methoxy-but-3-enyl)-tetrahydro-furan-3-ol (113643-23-5) → (3aR,4R,5S,7R,7aR)-3a-Hydroxy-7-methoxy-5-phenylsulfanyl-octahydro-benzofuran-4-carboxylic acid methyl ester (113643-25-7)

Guidance literature:

Multi-step reaction with 2 steps

2: 89 percent / trimethylaluminum / tetrahydrofuran / 0 °C

With trimethylaluminum; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)96669-3

upstream raw materials:

lithium thiophenoxide

(E)-(R)-5-Methoxy-5-((R)-3-oxo-tetrahydro-furan-2-yl)-pent-2-enoic acid methyl ester

(3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde

(2S,3S)-2-((R)-1-Methoxy-but-3-enyl)-tetrahydro-furan-3-ol