thioethyl 3,4-di-O-benzyl-2-O-pivaloyl-6-O-triisopropylsilyl-β-D-galactopyranoside-(1->4)-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside

Base Information

• Chemical Name: thioethyl 3,4-di-O-benzyl-2-O-pivaloyl-6-O-triisopropylsilyl-β-D-galactopyranoside-(1->4)-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside
• CAS No.: 196705-03-0
• Molecular Formula: C₆₁H₈₆O₁₂SSi
• Molecular Weight: 1071.5
• Mol file: 196705-03-0.mol

Synonyms:thioethyl 3,4-di-O-benzyl-2-O-pivaloyl-6-O-triisopropylsilyl-β-D-galactopyranoside-(1->4)-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside

Chemical Property of thioethyl 3,4-di-O-benzyl-2-O-pivaloyl-6-O-triisopropylsilyl-β-D-galactopyranoside-(1->4)-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of thioethyl 3,4-di-O-benzyl-2-O-pivaloyl-6-O-triisopropylsilyl-β-D-galactopyranoside-(1->4)-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside

There total 8 articles about thioethyl 3,4-di-O-benzyl-2-O-pivaloyl-6-O-triisopropylsilyl-β-D-galactopyranoside-(1->4)-3,6-di-O-benzyl-2-O-pivaloyl-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: 98.0%

pivaloyl chloride (3282-30-2) + thioethyl 3,4-di-O-benzyl-2-O-pivaloyl-6-O-triisopropylsilyl-β-D-galactopyranoside-(1->4)-3,6-di-O-benzyl-β-D-glucopyranoside (196705-02-9) → thioethyl 3,4-di-O-benzyl-2-O-pivaloyl-6-O-triisopropylsilyl-β-D-galactopyranoside-(1->4)-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside (196705-03-0)

Guidance literature:

With dmap; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1021/ja971640d

Reference yield:

pivaloyl chloride (3282-30-2) → thioethyl 3,4-di-O-benzyl-2-O-pivaloyl-6-O-triisopropylsilyl-β-D-galactopyranoside-(1->4)-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside (196705-03-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / DMAP / CH₂Cl₂ / 0.5 h / 20 °C

2: 86 percent / methyl triflate; di-tert-butylpyridine; 4 Angstroem molecular sieves / CH₂Cl₂ / 15 h / 0 °C

3: dimethyldioxirane / CH₂Cl₂; acetone / 0.33 h / 0 °C

4: trifluoroacetic acid anhydride / CH₂Cl₂ / 0.33 h / -78 °C

5: 98 percent / DMAP / CH₂Cl₂ / 0.5 h / 20 °C

With dmap; 4 A molecular sieve; 3,3-dimethyldioxirane; Di-tert-butylpyridine; trifluoroacetic anhydride; methyl trifluoromethanesulfonate; In dichloromethane; acetone; 1: Acylation / 2: glycosylation / 3: Epoxidation / 4: Ring cleavage / 5: Acylation;

DOI:10.1021/ja971640d

Reference yield:

3,4-di-O-benzyl-6-O-(triisopropylsilyl)-D-galactal (196703-96-5) → thioethyl 3,4-di-O-benzyl-2-O-pivaloyl-6-O-triisopropylsilyl-β-D-galactopyranoside-(1->4)-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside (196705-03-0)

Guidance literature:

Multi-step reaction with 7 steps

1: dimethyldioxirane / CH₂Cl₂; acetone / 0.33 h / 0 °C

2: trifluoroacetic acid anhydride / CH₂Cl₂ / 0.33 h / -78 °C

3: 100 percent / DMAP / CH₂Cl₂ / 0.5 h / 20 °C

4: 86 percent / methyl triflate; di-tert-butylpyridine; 4 Angstroem molecular sieves / CH₂Cl₂ / 15 h / 0 °C

5: dimethyldioxirane / CH₂Cl₂; acetone / 0.33 h / 0 °C

6: trifluoroacetic acid anhydride / CH₂Cl₂ / 0.33 h / -78 °C

7: 98 percent / DMAP / CH₂Cl₂ / 0.5 h / 20 °C

With dmap; 4 A molecular sieve; 3,3-dimethyldioxirane; Di-tert-butylpyridine; trifluoroacetic anhydride; methyl trifluoromethanesulfonate; In dichloromethane; acetone; 1: Epoxidation / 2: Ring cleavage / 3: Acylation / 4: glycosylation / 5: Epoxidation / 6: Ring cleavage / 7: Acylation;

DOI:10.1021/ja971640d

upstream raw materials:

pivaloyl chloride

thioethyl 3,4-di-O-benzyl-2-O-pivaloyl-6-O-triisopropylsilyl-β-D-galactopyranoside-(1->4)-3,6-di-O-benzyl-β-D-glucopyranoside

3,4-di-O-benzyl-6-O-(triisopropylsilyl)-D-galactal

thioethyl 3,4-di-O-benzyl-6-O-triisopropylsilyl-β-D-galactopyranoside

Downstream raw materials:

3,4-di-O-benzyl-2-O-pivaloyl-6-O-triisopropylsilyl-β-D-galactopyranoside-(1->4)-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside-(1->4)-3,6-di-O-benzyl-D-glucal