ethyl 3-O-acetyl-6-O-benzyl-1,2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: ethyl 3-O-acetyl-6-O-benzyl-1,2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside
• CAS No.: 263358-64-1
• Molecular Formula: C₂₅H₂₇NO₇S
• Molecular Weight: 485.558
• Mol file: 263358-64-1.mol

Synonyms:ethyl 3-O-acetyl-6-O-benzyl-1,2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside

Chemical Property of ethyl 3-O-acetyl-6-O-benzyl-1,2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 3-O-acetyl-6-O-benzyl-1,2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside

There total 6 articles about ethyl 3-O-acetyl-6-O-benzyl-1,2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside 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%

ethyl 3-O-acetyl-4,6-O-benzylidene-1,2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside (125520-04-9) → ethyl 3-O-acetyl-6-O-benzyl-1,2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside (263358-64-1)

Guidance literature:

With hydrogenchloride; 3 A molecular sieve; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; at 20 ℃; for 1h;

DOI:10.1080/07328300008544063

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose (10022-13-6,31505-44-9,81704-02-1,116347-84-3,131234-07-6,144300-04-9,79733-86-1) → ethyl 3-O-acetyl-6-O-benzyl-1,2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside (263358-64-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: BF₃*Et₂O / CH₂Cl₂ / 4.83 h / 0 - 20 °C

1.2: 74 percent / EtSH; TMSOTf / CH₂Cl₂ / 1.5 h / 20 °C

2.1: NaOMe / methanol / 2 h / 20 °C

3.1: 3.71 g / p-TsOH*H₂O / dimethylformamide / 70 °C

4.1: DMAP / pyridine / 1 h / 20 °C

5.1: 1.37 g / triethylsilane; TfOH; 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / -78 °C

With triethylsilane; dmap; trifluorormethanesulfonic acid; 4 A molecular sieve; boron trifluoride diethyl etherate; sodium methylate; toluene-4-sulfonic acid; In pyridine; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.200600515

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → ethyl 3-O-acetyl-6-O-benzyl-1,2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside (263358-64-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 3.71 g / p-TsOH*H₂O / dimethylformamide / 70 °C

2: DMAP / pyridine / 1 h / 20 °C

3: 1.37 g / triethylsilane; TfOH; 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / -78 °C

With triethylsilane; dmap; trifluorormethanesulfonic acid; 4 A molecular sieve; toluene-4-sulfonic acid; In pyridine; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.200600515

upstream raw materials:

ethyl 3-O-acetyl-4,6-O-benzylidene-1,2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose

benzaldehyde dimethyl acetal

ethyl-3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Downstream raw materials:

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