2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-β-D-mannopyranosyl-(1->4)-2-O-allyl-3,6-di-O-benzyl-β-D-galactopyranoside

Base Information

Chemical Name:2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-β-D-mannopyranosyl-(1->4)-2-O-allyl-3,6-di-O-benzyl-β-D-galactopyranoside
CAS No.:696599-10-7
Molecular Formula:C₅₅H₆₈O₁₁Si
Molecular Weight:933.224
Hs Code.:

Synonyms:2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-β-D-mannopyranosyl-(1->4)-2-O-allyl-3,6-di-O-benzyl-β-D-galactopyranoside

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Chemical Property of 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-β-D-mannopyranosyl-(1->4)-2-O-allyl-3,6-di-O-benzyl-β-D-galactopyranoside

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Technology Process of 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-β-D-mannopyranosyl-(1->4)-2-O-allyl-3,6-di-O-benzyl-β-D-galactopyranoside

There total 4 articles about 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-β-D-mannopyranosyl-(1->4)-2-O-allyl-3,6-di-O-benzyl-β-D-galactopyranoside 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: 68.0%

: 696599-04-9
2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-D-mannopyranosyl-(1->4)-2-O-allyl-3,6-di-O-benzyl-β-D-galactopyranoside

: 696599-10-7
2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-β-D-mannopyranosyl-(1->4)-2-O-allyl-3,6-di-O-benzyl-β-D-galactopyranoside

: {(2R,3R,4S,5S,6S)-6-[(2R,3S,4S,5R,6R)-5-Allyloxy-4-benzyloxy-2-benzyloxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yloxy]-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl}-methanol

Guidance literature:: With hydrogenchloride; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; at 0 ℃; for 0.5h; pH=2 - 3;
DOI:10.1081/SCC-120028645

Reference yield:

: 2-(trimethylsilyl)ethyl 4,6-O-benzylidene-3-O-benzyl-β-D-galactopyranoside

: 696599-10-7
2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-β-D-mannopyranosyl-(1->4)-2-O-allyl-3,6-di-O-benzyl-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 92 percent / NaH / dimethylformamide; various solvent(s) / 7 h / 20 °C

2: 70 percent / NaCNBH₃; hydrogen chloride; molecular sieves 3 Angstroem / tetrahydrofuran; diethyl ether / 0.75 h / 0 °C / pH 2 - 3

3: 69 percent / triethylsilyltrifluoromethane sulfonate; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.75 h / -45 °C

4: 68 percent / NaCNBH₃; hydrogen chloride / tetrahydrofuran; diethyl ether / 0.5 h / 0 °C / pH 2 - 3

With hydrogenchloride; 3 A molecular sieve; 4 A molecular sieve; triethylsilyl trifluoromethyl sulfonate; sodium hydride; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1081/SCC-120028645

Reference yield:

: 696598-87-5
2-(trimethylsilyl)ethyl 2-O-allyl-3-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside

: 696599-10-7
2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-β-D-mannopyranosyl-(1->4)-2-O-allyl-3,6-di-O-benzyl-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 70 percent / NaCNBH₃; hydrogen chloride; molecular sieves 3 Angstroem / tetrahydrofuran; diethyl ether / 0.75 h / 0 °C / pH 2 - 3

2: 69 percent / triethylsilyltrifluoromethane sulfonate; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.75 h / -45 °C

3: 68 percent / NaCNBH₃; hydrogen chloride / tetrahydrofuran; diethyl ether / 0.5 h / 0 °C / pH 2 - 3

With hydrogenchloride; 3 A molecular sieve; 4 A molecular sieve; triethylsilyl trifluoromethyl sulfonate; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1081/SCC-120028645