7-[5-acetoxy-3-benzoyloxy-6-benzoyloxymethyl-4-(3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-5-hydroxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-5-carboxylic acid 2-trimethylsilanyl-ethyl ester

Base Information

• Chemical Name: 7-[5-acetoxy-3-benzoyloxy-6-benzoyloxymethyl-4-(3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-5-hydroxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-5-carboxylic acid 2-trimethylsilanyl-ethyl ester
• CAS No.: 342824-28-6
• Molecular Formula: C₇₁H₈₂O₁₉Si
• Molecular Weight: 1267.51
• Mol file: 342824-28-6.mol

Synonyms:7-[5-acetoxy-3-benzoyloxy-6-benzoyloxymethyl-4-(3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-5-hydroxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-5-carboxylic acid 2-trimethylsilanyl-ethyl ester

Chemical Property of 7-[5-acetoxy-3-benzoyloxy-6-benzoyloxymethyl-4-(3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-5-hydroxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-5-carboxylic acid 2-trimethylsilanyl-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-[5-acetoxy-3-benzoyloxy-6-benzoyloxymethyl-4-(3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-5-hydroxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-5-carboxylic acid 2-trimethylsilanyl-ethyl ester

There total 7 articles about 7-[5-acetoxy-3-benzoyloxy-6-benzoyloxymethyl-4-(3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-5-hydroxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-5-carboxylic acid 2-trimethylsilanyl-ethyl 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: 71.0%

ethylthio 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1-3)-4-O-acetyl-2,6-di-O-benzoyl-β-D-galactopyranoside (203514-19-6) + 2-trimethylsilyl 3,4-O-isopropylidene quinate (342824-27-5) → 7-[5-acetoxy-3-benzoyloxy-6-benzoyloxymethyl-4-(3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-5-hydroxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-5-carboxylic acid 2-trimethylsilanyl-ethyl ester (342824-28-6)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; at -40 ℃; for 1h;

DOI:10.1016/S0040-4020(01)00195-8

Reference yield:

2-(Trimethylsilyl)ethanol (2916-68-9) → 7-[5-acetoxy-3-benzoyloxy-6-benzoyloxymethyl-4-(3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-5-hydroxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-5-carboxylic acid 2-trimethylsilanyl-ethyl ester (342824-28-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: HOBT; EDC; Et₃N / dimethylformamide / 1 h / 0 °C

1.2: dimethylformamide / 24 h / 20 °C

1.3: 0.48 mg / DDQ / CH₂Cl₂ / 2 h / 20 °C

2.1: 71 percent / NIS; TfOH / CH₂Cl₂ / 1 h / -40 °C

With N-iodo-succinimide; trifluorormethanesulfonic acid; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)00195-8

Reference yield:

methyl (1R,3R,4S,5R)-1,5-dihydroxy-3,4-(isopropylidenedioxy)cyclohexane-1-carboxylate (97373-88-1) → 7-[5-acetoxy-3-benzoyloxy-6-benzoyloxymethyl-4-(3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-5-hydroxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-5-carboxylic acid 2-trimethylsilanyl-ethyl ester (342824-28-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 70 percent / silfer triflate / CH₂Cl₂ / 3 h / 20 °C

2.1: 90 percent / NaOH / methanol; H₂O / 1 h / 20 °C

3.1: HOBT; EDC; Et₃N / dimethylformamide / 1 h / 0 °C

3.2: dimethylformamide / 24 h / 20 °C

3.3: 0.48 mg / DDQ / CH₂Cl₂ / 2 h / 20 °C

4.1: 71 percent / NIS; TfOH / CH₂Cl₂ / 1 h / -40 °C

With sodium hydroxide; N-iodo-succinimide; trifluorormethanesulfonic acid; silver trifluoromethanesulfonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)00195-8

upstream raw materials:

ethylthio 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1-3)-4-O-acetyl-2,6-di-O-benzoyl-β-D-galactopyranoside

2-trimethylsilyl 3,4-O-isopropylidene quinate

2-(Trimethylsilyl)ethanol

methyl (1R,3R,4S,5R)-1,5-dihydroxy-3,4-(isopropylidenedioxy)cyclohexane-1-carboxylate

Downstream raw materials:

7-[5-acetoxy-3-benzoyloxy-6-benzoyloxymethyl-4-(3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-5-hydroxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-5-carboxylic acid