Benzoic acid (1R,2R,3R)-2-benzyloxy-1-(bis-ethylsulfanyl-methyl)-3-methoxymethoxy-butyl ester

Base Information

• Chemical Name: Benzoic acid (1R,2R,3R)-2-benzyloxy-1-(bis-ethylsulfanyl-methyl)-3-methoxymethoxy-butyl ester
• CAS No.: 162210-59-5
• Molecular Formula: C₂₅H₃₄O₅S₂
• Molecular Weight: 478.674
• Mol file: 162210-59-5.mol

Synonyms:Benzoic acid (1R,2R,3R)-2-benzyloxy-1-(bis-ethylsulfanyl-methyl)-3-methoxymethoxy-butyl ester

Chemical Property of Benzoic acid (1R,2R,3R)-2-benzyloxy-1-(bis-ethylsulfanyl-methyl)-3-methoxymethoxy-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (1R,2R,3R)-2-benzyloxy-1-(bis-ethylsulfanyl-methyl)-3-methoxymethoxy-butyl ester

There total 4 articles about Benzoic acid (1R,2R,3R)-2-benzyloxy-1-(bis-ethylsulfanyl-methyl)-3-methoxymethoxy-butyl 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: 92.0%

chloromethyl methyl ether (107-30-2) + Benzoic acid (1R,2R,3R)-2-benzyloxy-1-(bis-ethylsulfanyl-methyl)-3-hydroxy-butyl ester → Benzoic acid (1R,2R,3R)-2-benzyloxy-1-(bis-ethylsulfanyl-methyl)-3-methoxymethoxy-butyl ester (162210-59-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; 0 deg C, 1 h and room t., 15 h;

DOI:10.1016/0040-4039(94)80021-9

Reference yield:

benzoyl chloride (98-88-4) → Benzoic acid (1R,2R,3R)-2-benzyloxy-1-(bis-ethylsulfanyl-methyl)-3-methoxymethoxy-butyl ester (162210-59-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / TEA / CH₂Cl₂ / 10 h / Ambient temperature

2: 87 percent / BF₃*Et₂O / CH₂Cl₂ / 3 h / -20 °C

3: 92 percent / Hunig's base / CH₂Cl₂ / 0 deg C, 1 h and room t., 15 h

With TEA; boron trifluoride diethyl etherate; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1016/0040-4039(94)80021-9

Reference yield:

(3R,4S,5R)-4-Benzyloxy-2-methoxy-5-methyl-tetrahydro-furan-3-ol → Benzoic acid (1R,2R,3R)-2-benzyloxy-1-(bis-ethylsulfanyl-methyl)-3-methoxymethoxy-butyl ester (162210-59-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / TEA / CH₂Cl₂ / 10 h / Ambient temperature

2: 87 percent / BF₃*Et₂O / CH₂Cl₂ / 3 h / -20 °C

3: 92 percent / Hunig's base / CH₂Cl₂ / 0 deg C, 1 h and room t., 15 h

With TEA; boron trifluoride diethyl etherate; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1016/0040-4039(94)80021-9

upstream raw materials:

chloromethyl methyl ether

benzoyl chloride

Benzoic acid (3R,4R,5R)-4-benzyloxy-2-methoxy-5-methyl-tetrahydro-furan-3-yl ester

Downstream raw materials:

Benzoic acid (1R,2R,3R)-2-benzyloxy-1-formyl-3-methoxymethoxy-butyl ester

(-)-Reiswigin A

(Z)-(2R,3S,4S,7R)-3-Benzyloxy-8-(2-isobutyl-[1,3]dioxolan-2-yl)-2-methoxymethoxy-7-methyl-oct-5-en-4-ol

(E)-(3R,6S,7R)-6-Benzyloxy-3-[(R)-2-(2-isobutyl-[1,3]dioxolan-2-yl)-1-methyl-ethyl]-7-methoxymethoxy-oct-4-enoic acid ethyl ester