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

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-β-D-glucopyranoside
CAS No.:196705-02-9
Molecular Formula:C₅₆H₇₈O₁₁SSi
Molecular Weight:987.38
Hs Code.:

Synonyms: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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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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-β-D-glucopyranoside

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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-β-D-glucopyranoside

There total 7 articles about 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 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:

: 75-08-1
ethanethiol

: 2,2-Dimethyl-propionic acid (2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-2-((1S,3R,4R,5S,6R)-5-benzyloxy-3-benzyloxymethyl-2,7-dioxa-bicyclo[4.1.0]hept-4-yloxy)-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-3-yl ester

: 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-β-D-glucopyranoside

Guidance literature:: With trifluoroacetic anhydride; In dichloromethane; at -78 ℃; for 0.333333h;
DOI:10.1021/ja971640d

Reference yield:

: 3282-30-2
pivaloyl chloride

: 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-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 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

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;
DOI:10.1021/ja971640d

Reference yield:

: 196703-96-5
3,4-di-O-benzyl-6-O-(triisopropylsilyl)-D-galactal

: 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-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 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

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;
DOI:10.1021/ja971640d