ethyl 3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: ethyl 3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside
• CAS No.: 419549-66-9
• Molecular Formula: C₂₆H₂₉NO₆S
• Molecular Weight: 483.585
• Mol file: 419549-66-9.mol

Synonyms:ethyl 3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside

Chemical Property of ethyl 3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside

There total 7 articles about ethyl 3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside 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%

2-((2S,3R,4R,6R)-4-Allyloxy-6-benzyloxymethyl-2-ethylsulfanyl-5-oxo-tetrahydro-pyran-3-yl)-isoindole-1,3-dione (860640-11-5) → ethyl 3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside (419549-66-9)

Guidance literature:

With L-Selectride; In tetrahydrofuran; at -10 ℃; for 0.166667h;

DOI:10.1081/CAR-200061584

Reference yield: 73.0%

ethyl 4-O-acetyl-3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside (419549-65-8) → ethyl 3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside (419549-66-9)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; methanol; for 4h;

DOI:10.1002/1521-3765(20020104)8:1<151::AID-CHEM151>3.0.CO;2-C

Reference yield:

ethyl 3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (419549-63-6) → ethyl 3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside (419549-66-9)

Guidance literature:

Multi-step reaction with 2 steps

1: N,N'-dicyclohexylcarbodiimide; pyridine; trifluoroacetic acid / CH₂Cl₂; dimethylsulfoxide

2: Zn(BH₄)2 / tetrahydrofuran; diethyl ether / 0.5 h / 0 °C

With pyridine; zinc(II) tetrahydroborate; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide;

DOI:10.1081/CAR-200061584

upstream raw materials:

ethyl 4-O-acetyl-3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside

2-((2S,3R,4R,6R)-4-Allyloxy-6-benzyloxymethyl-2-ethylsulfanyl-5-oxo-tetrahydro-pyran-3-yl)-isoindole-1,3-dione

ethyl 3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

2-((6S,7R,8aS)-6-ethylsulfanyl-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione

Downstream raw materials:

ethyl 3-O-allyl-4,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside

ethyl (3-O-acetyl-4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl)-(1->4)-[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)]-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

ethyl (3-O-acetyl-4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl)-(1->4)-3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

ethyl (3-O-acetyl-4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl)-(1->4)-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside