1,5-anhydro-4-O-(4-O-benzyl-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)-3-O-(tert-butyldimethylsilyl)-2,6-dideoxy-L-lyxo-hex-1-enitol

Base Information

Chemical Name:1,5-anhydro-4-O-(4-O-benzyl-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)-3-O-(tert-butyldimethylsilyl)-2,6-dideoxy-L-lyxo-hex-1-enitol
CAS No.:129985-33-7
Molecular Formula:C₂₅H₄₀O₅Si
Molecular Weight:448.675
Hs Code.:

Synonyms:1,5-anhydro-4-O-(4-O-benzyl-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)-3-O-(tert-butyldimethylsilyl)-2,6-dideoxy-L-lyxo-hex-1-enitol

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Chemical Property of 1,5-anhydro-4-O-(4-O-benzyl-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)-3-O-(tert-butyldimethylsilyl)-2,6-dideoxy-L-lyxo-hex-1-enitol

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Technology Process of 1,5-anhydro-4-O-(4-O-benzyl-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)-3-O-(tert-butyldimethylsilyl)-2,6-dideoxy-L-lyxo-hex-1-enitol

There total 9 articles about 1,5-anhydro-4-O-(4-O-benzyl-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)-3-O-(tert-butyldimethylsilyl)-2,6-dideoxy-L-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: 80.0%

: 129985-47-3
(2S,3S,4S)-3-((2S,5R,6S)-5-Benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-methyl-3,4-dihydro-2H-pyran-4-ol

: 18162-48-6
tert-butyldimethylsilyl chloride

: 129985-33-7
1,5-anhydro-4-O-(4-O-benzyl-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)-3-O-(tert-butyldimethylsilyl)-2,6-dideoxy-L-lyxo-hex-1-enitol

Guidance literature:: With 1H-imidazole; In dichloromethane; for 29h; Heating;
DOI:10.1021/ja00180a037

Reference yield:

: 100-39-0
benzyl bromide

: 129985-33-7
1,5-anhydro-4-O-(4-O-benzyl-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)-3-O-(tert-butyldimethylsilyl)-2,6-dideoxy-L-lyxo-hex-1-enitol

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) 60percent NaH in oil / 1.) THF, 30 min, 2.) RT, 14 h

2: 1.) 4-A molecular sieves, 2.) 90percent I(sym-collidine)2ClO₄ ⁽⁴⁾ / 1.) a.) CH₂Cl₂, RT, 30 min, b.) 0 deg C, 30 min, 2.) 0 deg C, 30 min

3: 57 percent / triphenyltin hydride, azobis(isobutyronitrile) / benzene / 0.5 h / Heating

4: 75 percent / lithium aluminum hydride / tetrahydrofuran; diethyl ether / 0.5 h / 0 °C

5: 80 percent / imidazole / CH₂Cl₂ / 29 h / Heating

With 1H-imidazole; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); iodonium(di-γ-collidine) perchlorate; 4 A molecular sieve; triphenylstannane; sodium hydride; In tetrahydrofuran; diethyl ether; dichloromethane; benzene;
DOI:10.1021/ja00180a037

Reference yield:

: 129985-30-4
1,5-anhydro-4-O-hydroxy-2,3,6-trideoxy-L-erythro-hex-1-enitol

: 129985-33-7
1,5-anhydro-4-O-(4-O-benzyl-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)-3-O-(tert-butyldimethylsilyl)-2,6-dideoxy-L-lyxo-hex-1-enitol

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) 60percent NaH in oil / 1.) THF, 30 min, 2.) RT, 14 h

2: 1.) 4-A molecular sieves, 2.) 90percent I(sym-collidine)2ClO₄ ⁽⁴⁾ / 1.) a.) CH₂Cl₂, RT, 30 min, b.) 0 deg C, 30 min, 2.) 0 deg C, 30 min

3: 57 percent / triphenyltin hydride, azobis(isobutyronitrile) / benzene / 0.5 h / Heating

4: 75 percent / lithium aluminum hydride / tetrahydrofuran; diethyl ether / 0.5 h / 0 °C

5: 80 percent / imidazole / CH₂Cl₂ / 29 h / Heating

With 1H-imidazole; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); iodonium(di-γ-collidine) perchlorate; 4 A molecular sieve; triphenylstannane; sodium hydride; In tetrahydrofuran; diethyl ether; dichloromethane; benzene;
DOI:10.1021/ja00180a037