1,5-anhydro-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-D-lyxo-hex-1-enitol

Base Information

Chemical Name:1,5-anhydro-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-D-lyxo-hex-1-enitol
CAS No.:500212-99-7
Molecular Formula:C₃₆H₄₆O₁₃Si
Molecular Weight:714.839
Hs Code.:

Synonyms:1,5-anhydro-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-D-lyxo-hex-1-enitol

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Chemical Property of 1,5-anhydro-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-D-lyxo-hex-1-enitol

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Technology Process of 1,5-anhydro-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-D-lyxo-hex-1-enitol

There total 5 articles about 1,5-anhydro-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-D-lyxo-hex-1-enitol 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: 69.0%

: 87316-22-1,137893-35-7
1,5-anhydro-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-lyxo-hex-1-enitol

: 86520-63-0
2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate

: 500212-99-7
1,5-anhydro-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-D-lyxo-hex-1-enitol

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at -78 ℃; for 5h;
DOI:10.1021/ol0514193

Reference yield: 35.0%

: 87316-22-1,137893-35-7
1,5-anhydro-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-lyxo-hex-1-enitol

: 74808-10-9,86520-63-0,87119-53-7,92052-29-4,121238-27-5,142831-80-9,127061-80-7
2,3,4,6-tetra-O-acetyl-D-galactopyranosyl trichloroacetimidate

: 500212-99-7
1,5-anhydro-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-D-lyxo-hex-1-enitol

Guidance literature:: With 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; at -80 ℃; for 0.5h;
DOI:10.1023/A:1020428329743

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 500212-99-7
1,5-anhydro-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-D-lyxo-hex-1-enitol

Guidance literature:: Multi-step reaction with 2 steps

1: 80 percent / 4-dimethylaminopyridine; triethylamine / dimethylformamide / 0 - 20 °C

2: 35 percent / molecular sieves MS-4 Angstroem; BF₃*Et₂O / CH₂Cl₂ / 0.5 h / -80 °C

With dmap; 4 A molecular sieve; boron trifluoride diethyl etherate; triethylamine; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1023/A:1020428329743