2-((2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yloxymethyl)-benzoic acid

Base Information

• Chemical Name: 2-((2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yloxymethyl)-benzoic acid
• CAS No.: 328936-93-2
• Molecular Formula: C₃₇H₄₀O₇S
• Molecular Weight: 628.786
• Mol file: 328936-93-2.mol

Synonyms:2-((2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yloxymethyl)-benzoic acid

Chemical Property of 2-((2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yloxymethyl)-benzoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-((2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yloxymethyl)-benzoic acid

There total 2 articles about 2-((2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yloxymethyl)-benzoic acid 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: 82.0%

ethyl 3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside (180187-58-0) + 2-(bromomethyl)benzoic acid t-butyl ester (105340-30-5) → 2-((2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yloxymethyl)-benzoic acid (328936-93-2)

Guidance literature:

ethyl 3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside; 2-(bromomethyl)benzoic acid t-butyl ester; With sodium hydride; In N,N-dimethyl-formamide; at 25 ℃; for 1h;

With trifluoroacetic acid; In dichloromethane; at 25 ℃; for 3h;

DOI:10.1016/S0040-4039(00)02032-3

Reference yield:

2-(bromomethyl)benzoic acid (7115-89-1) → 2-((2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yloxymethyl)-benzoic acid (328936-93-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 77 percent / BF₃ etherate / CH₂Cl₂ / 25 °C

2.1: NaH / dimethylformamide / 1 h / 25 °C

2.2: 82 percent / CF₃COOH / CH₂Cl₂ / 3 h / 25 °C

With boron trifluoride diethyl etherate; sodium hydride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)02032-3

Reference yield:

methyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside (76375-66-1) + 2-((2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yloxymethyl)-benzoic acid (328936-93-2) → 2-((2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yloxymethyl)-benzoic acid (2R,4aR,6S,7R,8S,8aR)-7-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 25 ℃; for 18h;

DOI:10.1016/S0040-4039(00)02032-3

upstream raw materials:

ethyl 3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

2-(bromomethyl)benzoic acid t-butyl ester

2-(bromomethyl)benzoic acid

Downstream raw materials:

2-((2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yloxymethyl)-benzoic acid (2S,3R,4S,5R,6R)-3-benzyloxy-6-benzyloxymethyl-5-hydroxy-2-methoxy-tetrahydro-pyran-4-yl ester