1,5-anhydro-3,4-di-O-(tert-butyldimethylsilyl)-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-lyxo-hex-1-enopyranose

Base Information

Chemical Name:1,5-anhydro-3,4-di-O-(tert-butyldimethylsilyl)-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-lyxo-hex-1-enopyranose
CAS No.:336130-11-1
Molecular Formula:C₃₄H₅₆O₄Si₃
Molecular Weight:613.073
Hs Code.:

Synonyms:1,5-anhydro-3,4-di-O-(tert-butyldimethylsilyl)-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-lyxo-hex-1-enopyranose

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Chemical Property of 1,5-anhydro-3,4-di-O-(tert-butyldimethylsilyl)-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-lyxo-hex-1-enopyranose

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Technology Process of 1,5-anhydro-3,4-di-O-(tert-butyldimethylsilyl)-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-lyxo-hex-1-enopyranose

There total 1 articles about 1,5-anhydro-3,4-di-O-(tert-butyldimethylsilyl)-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-lyxo-hex-1-enopyranose 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: 93.0%

: 69739-34-0
t-butyldimethylsiyl triflate

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

: 336130-11-1
1,5-anhydro-3,4-di-O-(tert-butyldimethylsilyl)-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-lyxo-hex-1-enopyranose

Guidance literature:: With pyridine; In tetrahydrofuran; at 0 - 20 ℃; for 24.5h;
DOI:10.1021/jo001512z

Reference yield: 80.0%

: 336130-11-1
1,5-anhydro-3,4-di-O-(tert-butyldimethylsilyl)-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-lyxo-hex-1-enopyranose

: 3,4-di-O-(tert-butyldimethylsilyl)-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-galactopyranose

Guidance literature:: With water; triphenylphosphine hydrobromide; In tetrahydrofuran; at 20 ℃; for 6h;
DOI:10.1021/jo001512z

Reference yield:

: 336130-11-1
1,5-anhydro-3,4-di-O-(tert-butyldimethylsilyl)-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-lyxo-hex-1-enopyranose

: (2R,3S,4R,5R,6S,8R,4'R)-5-azido-8-(3'-tert-butoxycarbonyl-2',2'-dimethyloxazolidin-4'-yl)-3,4-di-tert-butyldimethylsilyloxy-2-tert-butyldiphenylsilyloxymethyl-1,7-dioxaspiro[5.5]undec-10-ene

Guidance literature:: Multi-step reaction with 6 steps

1.1: 80 percent / H₂O; PPh₃*HBr / tetrahydrofuran / 6 h / 20 °C

2.1: 92 percent / PCC; NaOAc; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / 20 °C

3.1: KHMDS / tetrahydrofuran / 0.75 h / -78 °C

3.2: trisyl-N₃ / tetrahydrofuran / 0.08 h / -96 °C

3.3: 56 percent / AcOH / tetrahydrofuran / 1 h / -96 - 20 °C

4.1: TMEDA; n-BuLi / tetrahydrofuran; hexane / 1.5 h / -78 °C

4.2: 62 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C

5.1: 45 percent / H₂ / Pd/C / ethyl acetate; methanol / 48 h / 20 °C / 690 Torr

6.1: 51 percent / CSA / CH₂Cl₂ / 20 h / 20 °C

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; 4 A molecular sieve; camphor-10-sulfonic acid; water; hydrogen; sodium acetate; triphenylphosphine hydrobromide; potassium hexamethylsilazane; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate;
DOI:10.1021/jo001512z