(S)-3-(6-Benzyloxymethyl-tetrahydro-pyran-2-yloxy)-2-(toluene-4-sulfonylamino)-propionic acid methyl ester

Base Information

• Chemical Name: (S)-3-(6-Benzyloxymethyl-tetrahydro-pyran-2-yloxy)-2-(toluene-4-sulfonylamino)-propionic acid methyl ester
• CAS No.: 294844-18-1
• Molecular Formula: C₂₄H₃₁NO₇S
• Molecular Weight: 477.579
• Mol file: 294844-18-1.mol

Synonyms:(S)-3-(6-Benzyloxymethyl-tetrahydro-pyran-2-yloxy)-2-(toluene-4-sulfonylamino)-propionic acid methyl ester

Chemical Property of (S)-3-(6-Benzyloxymethyl-tetrahydro-pyran-2-yloxy)-2-(toluene-4-sulfonylamino)-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-(6-Benzyloxymethyl-tetrahydro-pyran-2-yloxy)-2-(toluene-4-sulfonylamino)-propionic acid methyl ester

There total 2 articles about (S)-3-(6-Benzyloxymethyl-tetrahydro-pyran-2-yloxy)-2-(toluene-4-sulfonylamino)-propionic 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: 83.0%

methyl (2S)-3-hydroxy-2-{[(4-methylphenyl)sulfonyl]amino}propanoate (17136-46-8) + 2-((benzyloxy)methyl)-3,4-dihydro-2H-pyran (194861-23-9) → (S)-3-(6-Benzyloxymethyl-tetrahydro-pyran-2-yloxy)-2-(toluene-4-sulfonylamino)-propionic acid methyl ester (294844-18-1)

Guidance literature:

With pyridinium p-toluenesulfonate; In 1,2-dichloro-ethane; at 75 ℃; for 16h;

DOI:10.1016/S0040-4039(00)00710-3

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → (S)-3-(6-Benzyloxymethyl-tetrahydro-pyran-2-yloxy)-2-(toluene-4-sulfonylamino)-propionic acid methyl ester (294844-18-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydroxide / water; ethyl acetate

1.2: HCl

2.1: pyridinium p-toluenesulfonate / 1,2-dichloro-ethane / 16 h / 75 °C

With sodium hydroxide; pyridinium p-toluenesulfonate; In water; ethyl acetate; 1,2-dichloro-ethane; 1.1: Tosylation / 1.2: Esterification / 2.1: Etherification;

DOI:10.1016/S0040-4039(00)00710-3

Reference yield: 95.0%

(E)-5-[(tert-butyldiphenylsilyl)oxy]pent-3-en-1-ol (292157-32-5) + (S)-3-(6-Benzyloxymethyl-tetrahydro-pyran-2-yloxy)-2-(toluene-4-sulfonylamino)-propionic acid methyl ester (294844-18-1) → (S)-3-(6-Benzyloxymethyl-tetrahydro-pyran-2-yloxy)-2-[[(E)-5-(tert-butyl-diphenyl-silanyloxy)-pent-3-enyl]-(toluene-4-sulfonyl)-amino]-propionic acid methyl ester (294844-19-2)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1016/S0040-4039(00)00710-3

upstream raw materials:

methyl (2S)-3-hydroxy-2-{[(4-methylphenyl)sulfonyl]amino}propanoate

2-((benzyloxy)methyl)-3,4-dihydro-2H-pyran

p-toluenesulfonyl chloride

Downstream raw materials:

(S)-3-(6-Benzyloxymethyl-tetrahydro-pyran-2-yloxy)-2-[[(E)-5-(tert-butyl-diphenyl-silanyloxy)-pent-3-enyl]-(toluene-4-sulfonyl)-amino]-propionic acid methyl ester

(E)-(R)-3-(6-Benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-4-(toluene-4-sulfonyl)-1-oxa-4-aza-cyclotetradec-7-ene-10,10-dicarboxylic acid dimethyl ester

2-(4-{(R)-3-(6-Benzyloxymethyl-tetrahydro-pyran-2-yloxy)-2-[((E)-5-hydroxy-pent-3-enyl)-(toluene-4-sulfonyl)-amino]-propoxy}-butyl)-malonic acid dimethyl ester

(E)-(S)-3-(6-Benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-14-oxo-4-(toluene-4-sulfonyl)-1-oxa-4-aza-cyclotetradec-7-ene-10,10-dicarboxylic acid dimethyl ester