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

Base Information

• Chemical Name: 1,5-anhydro-3-O-benzoyl-4-O-<4-O-(4-O-benzyl-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)-3-O-(tert-butyldimethylsilyl)-2,6-dideoxy-α-L-lyxo-hexopyranosyl>-2,6-dideoxy-L-lyxo-hex-1-enitol
• CAS No.: 129985-34-8
• Molecular Formula: C₃₈H₅₄O₉Si
• Molecular Weight: 682.927
• Mol file: 129985-34-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about 1,5-anhydro-3-O-benzoyl-4-O-<4-O-(4-O-benzyl-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)-3-O-(tert-butyldimethylsilyl)-2,6-dideoxy-α-L-lyxo-hexopyranosyl>-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: 93.0%

Benzoic acid (2S,3R,4S)-3-[(2S,3R,4R,5R,6S)-5-((2S,5R,6S)-5-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-(tert-butyl-dimethyl-silanyloxy)-3-iodo-6-methyl-tetrahydro-pyran-2-yloxy]-2-methyl-3,4-dihydro-2H-pyran-4-yl ester (129985-48-4) → 1,5-anhydro-3-O-benzoyl-4-O-<4-O-(4-O-benzyl-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)-3-O-(tert-butyldimethylsilyl)-2,6-dideoxy-α-L-lyxo-hexopyranosyl>-2,6-dideoxy-L-lyxo-hex-1-enitol (129985-34-8)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); triphenylstannane; In benzene; for 0.5h; Heating;

DOI:10.1021/ja00180a037

Reference yield:

1,5-anhydro-4-O-hydroxy-2,3,6-trideoxy-L-erythro-hex-1-enitol (129985-30-4) → 1,5-anhydro-3-O-benzoyl-4-O-<4-O-(4-O-benzyl-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)-3-O-(tert-butyldimethylsilyl)-2,6-dideoxy-α-L-lyxo-hexopyranosyl>-2,6-dideoxy-L-lyxo-hex-1-enitol (129985-34-8)

Guidance literature:

Multi-step reaction with 7 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

6: 1.) 4-A molecular sieves, 2.) 90percent I(sym-collidine)2ClO₄ ⁽⁴⁾ / 1.) a.) CH₂Cl₂, RT, 30 min, b.) -78 deg C, 30 min, 2.) -78 deg C, 30 min

7: 93 percent / triphenyltin hydride, azobis(isobutyronitrile) / benzene / 0.5 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:

benzyl bromide (100-39-0) → 1,5-anhydro-3-O-benzoyl-4-O-<4-O-(4-O-benzyl-2,3,6-trideoxy-α-L-arabino-hexopyranosyl)-3-O-(tert-butyldimethylsilyl)-2,6-dideoxy-α-L-lyxo-hexopyranosyl>-2,6-dideoxy-L-lyxo-hex-1-enitol (129985-34-8)

Guidance literature:

Multi-step reaction with 7 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

6: 1.) 4-A molecular sieves, 2.) 90percent I(sym-collidine)2ClO₄ ⁽⁴⁾ / 1.) a.) CH₂Cl₂, RT, 30 min, b.) -78 deg C, 30 min, 2.) -78 deg C, 30 min

7: 93 percent / triphenyltin hydride, azobis(isobutyronitrile) / benzene / 0.5 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

upstream raw materials:

Benzoic acid (2S,3R,4S)-3-[(2S,3R,4R,5R,6S)-5-((2S,5R,6S)-5-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-(tert-butyl-dimethyl-silanyloxy)-3-iodo-6-methyl-tetrahydro-pyran-2-yloxy]-2-methyl-3,4-dihydro-2H-pyran-4-yl ester

benzyl bromide

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

(2S,3R)-3-benzyloxy-2-methyl-3,4-dihydro-2H-pyran

Downstream raw materials:

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

(2S,3S,4S)-3-[(2S,4S,5R,6S)-5-((2S,5R,6S)-5-Benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-2-methyl-3,4-dihydro-2H-pyran-4-ol