phenyl 2-O-[3-O-tertbutyldimethylsilyl-4,6-O-(di-tert-butylsilanediyl)-2-O-pivaloyl-α-D-mannopyranosyl]-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

Base Information

Chemical Name:phenyl 2-O-[3-O-tertbutyldimethylsilyl-4,6-O-(di-tert-butylsilanediyl)-2-O-pivaloyl-α-D-mannopyranosyl]-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside
CAS No.:1345819-47-7
Molecular Formula:C₅₈H₈₂O₁₁SSi₂
Molecular Weight:1043.52
Hs Code.:

phenyl 2-O-[3-O-tertbutyldimethylsilyl-4,6-O-(di-tert-butylsilanediyl)-2-O-pivaloyl-α-D-mannopyranosyl]-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

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Chemical Property of phenyl 2-O-[3-O-tertbutyldimethylsilyl-4,6-O-(di-tert-butylsilanediyl)-2-O-pivaloyl-α-D-mannopyranosyl]-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

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Technology Process of phenyl 2-O-[3-O-tertbutyldimethylsilyl-4,6-O-(di-tert-butylsilanediyl)-2-O-pivaloyl-α-D-mannopyranosyl]-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

There total 8 articles about phenyl 2-O-[3-O-tertbutyldimethylsilyl-4,6-O-(di-tert-butylsilanediyl)-2-O-pivaloyl-α-D-mannopyranosyl]-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside 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:

: C₂₇H₅₀Cl₃NO₇Si₂

: 127299-77-8
phenyl 3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

: 1345819-47-7
phenyl 2-O-[3-O-tertbutyldimethylsilyl-4,6-O-(di-tert-butylsilanediyl)-2-O-pivaloyl-α-D-mannopyranosyl]-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

Guidance literature:: C₂₇H₅₀Cl₃NO₇Si₂; phenyl 3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside; In dichloromethane; at 20 ℃; for 0.5h; Molecular sieve;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -20 ℃; for 2h; Molecular sieve;
DOI:10.1021/jo201165v

Reference yield:

: 18395-90-9
Di-tert-butyldichlorosilane

: 1345819-47-7
phenyl 2-O-[3-O-tertbutyldimethylsilyl-4,6-O-(di-tert-butylsilanediyl)-2-O-pivaloyl-α-D-mannopyranosyl]-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1.1: 2,6-dimethylpyridine / N,N-dimethyl-formamide

2.1: dichloromethane / 1 h / 20 °C

3.1: 1H-imidazole / N,N-dimethyl-formamide

4.1: dmap / dichloromethane / 2 h

5.1: ethanolamine / ethyl acetate / 2 h / 20 °C

6.1: dichloromethane / 0.17 h / 20 °C / Molecular sieve

6.2: 0.75 h / Molecular sieve

7.1: dichloromethane / 0.5 h / 20 °C / Molecular sieve

7.2: 2 h / -20 °C / Molecular sieve

With 1H-imidazole; 2,6-dimethylpyridine; dmap; ethanolamine; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jo201165v

Reference yield:

: 3282-30-2
pivaloyl chloride

: 1345819-47-7
phenyl 2-O-[3-O-tertbutyldimethylsilyl-4,6-O-(di-tert-butylsilanediyl)-2-O-pivaloyl-α-D-mannopyranosyl]-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: dmap / dichloromethane / 2 h

2.1: ethanolamine / ethyl acetate / 2 h / 20 °C

3.1: dichloromethane / 0.17 h / 20 °C / Molecular sieve

3.2: 0.75 h / Molecular sieve

4.1: dichloromethane / 0.5 h / 20 °C / Molecular sieve

4.2: 2 h / -20 °C / Molecular sieve

With dmap; ethanolamine; In dichloromethane; ethyl acetate;
DOI:10.1021/jo201165v