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

Base Information

• Chemical Name: ethyl 4-O-acetyl-3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside
• CAS No.: 419549-65-8
• Molecular Formula: C₂₈H₃₁NO₇S
• Molecular Weight: 525.623
• Mol file: 419549-65-8.mol

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

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

There total 5 articles about ethyl 4-O-acetyl-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: 65.0%

sodium acetate (127-09-3) + ethyl 3-O-allyl-6-O-benzyl-2-deoxy-4-O-mesyl-2-phthalimido-1-thio-β-D-glucopyranoside (854911-47-0) → ethyl 4-O-acetyl-3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside (419549-65-8)

Guidance literature:

In dimethyl sulfoxide; at 130 ℃; for 24h;

DOI:10.1135/cccc20041914

Reference yield:

ethyl 3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (419549-63-6) → ethyl 4-O-acetyl-3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside (419549-65-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / pyridine / 24 h / 20 °C

2: 65 percent / dimethylsulfoxide / 24 h / 130 °C

With pyridine; In dimethyl sulfoxide;

DOI:10.1135/cccc20041914

Reference yield:

2-((6S,7R,8aS)-6-ethylsulfanyl-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione (129519-28-4) → ethyl 4-O-acetyl-3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside (419549-65-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / NaH / tetrahydrofuran

2: 85 percent / BH₃*Me₃N; 4 Angstroem molecular sieves; AlCl₃ / tetrahydrofuran / 6 h / 20 °C

3: pyridine / CH₂Cl₂ / 2 h / 0 °C

4: 1.08 g / CH₂Cl₂; dimethylformamide / 5 h / 0 °C

With pyridine; aluminium trichloride; trimethylamine-borane; 4 A molecular sieve; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

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

upstream raw materials:

tetrabutylammonium acetate

Trifluoro-methanesulfonic acid (2R,3S,4R,5R,6S)-4-allyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yl ester

sodium acetate

ethyl 3-O-allyl-6-O-benzyl-2-deoxy-4-O-mesyl-2-phthalimido-1-thio-β-D-glucopyranoside

Downstream raw materials:

pent-4-enyl 4-O-acetyl-3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-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