propanedioic acid, <2-(benzyloxy)-2,3-dihydro-6H-pyran-3-yl>-2-propynyl-dimethyl ester

Base Information

• Chemical Name: propanedioic acid, <2-(benzyloxy)-2,3-dihydro-6H-pyran-3-yl>-2-propynyl-dimethyl ester
• CAS No.: 160977-65-1
• Molecular Formula: C₂₀H₂₂O₆
• Molecular Weight: 358.391
• Mol file: 160977-65-1.mol

Synonyms:propanedioic acid, <2-(benzyloxy)-2,3-dihydro-6H-pyran-3-yl>-2-propynyl-dimethyl ester

Chemical Property of propanedioic acid, <2-(benzyloxy)-2,3-dihydro-6H-pyran-3-yl>-2-propynyl-dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of propanedioic acid, <2-(benzyloxy)-2,3-dihydro-6H-pyran-3-yl>-2-propynyl-dimethyl ester

There total 10 articles about propanedioic acid, <2-(benzyloxy)-2,3-dihydro-6H-pyran-3-yl>-2-propynyl-dimethyl 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: 76.0%

dimethyl (prop-2-yn-1-yl)malonate (95124-07-5) + benzyl 2,3,4-trideoxy-4-chloro-β-L-glycero-pent-2-enopyranoside (160977-63-9) → propanedioic acid, <2-(benzyloxy)-2,3-dihydro-6H-pyran-3-yl>-2-propynyl-dimethyl ester (160977-65-1)

Guidance literature:

With sodium hydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 0 ℃;

DOI:10.1016/S0040-4039(00)78441-3

Reference yield:

benzyl 4-O-acetyl-2,3-dideoxy-α-D-glycero-pent-2-enopyranoside (71978-99-9) → propanedioic acid, <2-(benzyloxy)-2,3-dihydro-6H-pyran-3-yl>-2-propynyl-dimethyl ester (160977-65-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.24 g / triethylamine / methanol; H₂O / 4 h / Ambient temperature

2: 94 percent / p-toluenesulfonyl chloride, pyridine / 50 °C / 3-4 h

3: 1.) NaH, 2.) triphenylphosphine, tetrakis(triphenylphosphine)palladium⁽⁰⁾ / 1.) THF, 0 deg C, 20 min, 2.) THF, 0 deg C, 1 h

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydride; triethylamine; p-toluenesulfonyl chloride; triphenylphosphine; In methanol; water;

DOI:10.1021/jo951298s

Reference yield:

benzyl 2-O-p-tosyl-3,4-anhydro-β-L-arabinopyranoside (113489-63-7) → propanedioic acid, <2-(benzyloxy)-2,3-dihydro-6H-pyran-3-yl>-2-propynyl-dimethyl ester (160977-65-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / sodium iodide, sodium acetate, acetic acid / acetone / Heating; 4-5 h

2: 70 percent / POCl₃, pyridine / -40 - 0 °C

3: 1.) NaH, 2.) triphenylphosphine, tetrakis(triphenylphosphine)palladium⁽⁰⁾ / 1.) THF, 0 deg C, 20 min, 2.) THF, reflux, 1 h

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium acetate; sodium hydride; acetic acid; triphenylphosphine; sodium iodide; trichlorophosphate; In acetone;

DOI:10.1021/jo951298s

upstream raw materials:

dimethyl (prop-2-yn-1-yl)malonate

benzyl 2,3,4-trideoxy-4-chloro-β-L-glycero-pent-2-enopyranoside

benzyl 2-O-p-tosyl-3,4-dideoxy-α-D-glycero-pent-3-enopyranoside

sodium dimethylpropargylmalonate