(2-trimethylsilyl) O-(2,3-di-O-benzoyl-6-O-benzyl-β-D-[13C6]galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-β-D-[¹³C₆]glucopyranoside

Base Information

• Chemical Name: (2-trimethylsilyl) O-(2,3-di-O-benzoyl-6-O-benzyl-β-D-[13C6]galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-β-D-[¹³C₆]glucopyranoside
• CAS No.: 213020-79-2
• Molecular Formula: C₅₉H₆₆O₁₃Si
• Molecular Weight: 1023.12

Synonyms:(2-trimethylsilyl) O-(2,3-di-O-benzoyl-6-O-benzyl-β-D-[13C6]galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-β-D-[¹³C₆]glucopyranoside

Chemical Property of (2-trimethylsilyl) O-(2,3-di-O-benzoyl-6-O-benzyl-β-D-[13C6]galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-β-D-[¹³C₆]glucopyranoside

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Technology Process of (2-trimethylsilyl) O-(2,3-di-O-benzoyl-6-O-benzyl-β-D-[13C6]galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-β-D-[¹³C₆]glucopyranoside

There total 5 articles about (2-trimethylsilyl) O-(2,3-di-O-benzoyl-6-O-benzyl-β-D-[13C6]galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-β-D-[¹³C₆]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: 87.0%

(2-trimethylsilyl) O-(2,3-di-O-benzoyl-6-O-benzyl-4-O-levulinoyl-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-β-D-[13C12]glucopyranoside (213020-78-1) → (2-trimethylsilyl) O-(2,3-di-O-benzoyl-6-O-benzyl-β-D-[13C6]galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-β-D-[13C6]glucopyranoside (213020-79-2)

Guidance literature:

With methanol; hydrazinium monoacetate; at 0 - 20 ℃; for 18h;

DOI:10.1016/S0040-4020(98)00577-8

Reference yield:

methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-[13C6]glucopyranoside → (2-trimethylsilyl) O-(2,3-di-O-benzoyl-6-O-benzyl-β-D-[13C6]galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-β-D-[13C6]glucopyranoside (213020-79-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 92 percent / triethylsilane; trifluoroacetic acid / CH₂Cl₂ / 5 h / 0 - 20 °C

2: 91 percent / pyridine / 4-DMAP / 14 h / 70 °C

3: 99 percent / 18-crown-6 / toluene / 18 h / Heating

4: 84 percent / N-(phenylseleno)phthalimide; CF₃CO₂Si(CH₃)3 / CH₂Cl₂ / 1 h / 0 °C

5: 87 percent / NH₂NH₂*AcOH; MeOH / 18 h / 0 - 20 °C

With pyridine; methanol; triethylsilane; N-phenylselanylphthalimide; 18-crown-6 ether; trimethylsilyl trifluoroacetate; hydrazinium monoacetate; trifluoroacetic acid; dmap; In dichloromethane; toluene; 1: Ring cleavage / 2: Acylation / 3: Acylation / 4: Condensation / 5: Hydrolysis;

DOI:10.1016/S0040-4020(98)00577-8

Reference yield:

methyl 2,3-di-O-benzoyl-6-O-benzyl-1-thio-β-D-[13C6]glucopyranoside (213020-72-5) → (2-trimethylsilyl) O-(2,3-di-O-benzoyl-6-O-benzyl-β-D-[13C6]galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-β-D-[13C6]glucopyranoside (213020-79-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 91 percent / pyridine / 4-DMAP / 14 h / 70 °C

2: 99 percent / 18-crown-6 / toluene / 18 h / Heating

3: 84 percent / N-(phenylseleno)phthalimide; CF₃CO₂Si(CH₃)3 / CH₂Cl₂ / 1 h / 0 °C

4: 87 percent / NH₂NH₂*AcOH; MeOH / 18 h / 0 - 20 °C

With pyridine; methanol; N-phenylselanylphthalimide; 18-crown-6 ether; trimethylsilyl trifluoroacetate; hydrazinium monoacetate; dmap; In dichloromethane; toluene; 1: Acylation / 2: Acylation / 3: Condensation / 4: Hydrolysis;

DOI:10.1016/S0040-4020(98)00577-8

upstream raw materials:

(2-trimethylsilyl) O-(2,3-di-O-benzoyl-6-O-benzyl-4-O-levulinoyl-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzyl-β-D-[13C12]glucopyranoside

methyl 2,3-di-O-benzoyl-6-O-benzyl-1-thio-β-D-[13C6]glucopyranoside

methyl 2,3,6-di-O-benzyl-4-O-levulinoyl-1-thio-β-D-[13C6]galactopyranoside

methyl 2,3-di-O-benzoyl-6-O-benzyl-4-(4-bromobenzenesufonyl)-1-thio-β-D-[13C6]glucopyranoside

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