2-(Trimethylsilyl)ethyl 2,6-di-O-benzyl-3-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-ribo-hexopyranoside

Base Information

Chemical Name:2-(Trimethylsilyl)ethyl 2,6-di-O-benzyl-3-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-ribo-hexopyranoside
CAS No.:152771-05-6
Molecular Formula:C₃₉H₅₄O₁₄Si
Molecular Weight:774.935
Hs Code.:

Synonyms:2-(Trimethylsilyl)ethyl 2,6-di-O-benzyl-3-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-ribo-hexopyranoside

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Chemical Property of 2-(Trimethylsilyl)ethyl 2,6-di-O-benzyl-3-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-ribo-hexopyranoside

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Technology Process of 2-(Trimethylsilyl)ethyl 2,6-di-O-benzyl-3-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-ribo-hexopyranoside

There total 4 articles about 2-(Trimethylsilyl)ethyl 2,6-di-O-benzyl-3-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-ribo-hexopyranoside 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: 71.0%

: 2-(Trimethylsilyl)ethyl 2,6-di-O-benzyl-3-deoxy-β-D-ribo-hexopyranoside

: 3068-32-4
1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

: 152771-05-6
2-(Trimethylsilyl)ethyl 2,6-di-O-benzyl-3-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-ribo-hexopyranoside

Guidance literature:: With silver silicate; 3 A molecular sieve; In dichloromethane; for 17h; Ambient temperature;
DOI:10.1016/0008-6215(93)84028-5

Reference yield:

: 152770-96-2
2-(Trimethylsilyl)ethyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-β-D-ribo-hexopyranoside

: 152771-05-6
2-(Trimethylsilyl)ethyl 2,6-di-O-benzyl-3-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-ribo-hexopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 75 percent / NaBH₃CN, ether. HCl, mol. sieves 3 Angstroem / tetrahydrofuran / 0.08 h

2: 71 percent / silver silicate, mol. sieves 3 Angstroem / CH₂Cl₂ / 17 h / Ambient temperature

With hydrogenchloride; silver silicate; 3 A molecular sieve; sodium cyanoborohydride; In tetrahydrofuran; dichloromethane;
DOI:10.1016/0008-6215(93)84028-5

Reference yield:

: (2R,4aR,6R,7R,8S,8aS)-7-Benzyloxy-2-phenyl-6-(2-trimethylsilanyl-ethoxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

: 152771-05-6
2-(Trimethylsilyl)ethyl 2,6-di-O-benzyl-3-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-ribo-hexopyranoside

Guidance literature:: Multi-step reaction with 4 steps

2: 98 percent / Bu₃SnH, AIBN / toluene / Heating

3: 75 percent / NaBH₃CN, ether. HCl, mol. sieves 3 Angstroem / tetrahydrofuran / 0.08 h

4: 71 percent / silver silicate, mol. sieves 3 Angstroem / CH₂Cl₂ / 17 h / Ambient temperature

With hydrogenchloride; 2,2'-azobis(isobutyronitrile); silver silicate; 3 A molecular sieve; tri-n-butyl-tin hydride; sodium cyanoborohydride; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1016/0008-6215(93)84028-5