L-arabino-Hex-5-enitol, 2,6-anhydro-1,5-dideoxy-, 4-benzoate

Base Information

• Chemical Name: L-arabino-Hex-5-enitol, 2,6-anhydro-1,5-dideoxy-, 4-benzoate
• CAS No.: 130061-11-9
• Molecular Formula: C₁₃H₁₄O₄
• Molecular Weight: 234.252
• DSSTox Substance ID: DTXSID901185513
• Mol file: 130061-11-9.mol

Synonyms:DTXSID901185513;L-arabino-Hex-5-enitol, 2,6-anhydro-1,5-dideoxy-, 4-benzoate;130061-11-9

Chemical Property of L-arabino-Hex-5-enitol, 2,6-anhydro-1,5-dideoxy-, 4-benzoate

Chemical Property:

• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 234.08920892
• Heavy Atom Count: 17
• Complexity: 294

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1C(C(C=CO1)OC(=O)C2=CC=CC=C2)O
• Isomeric SMILES: C[C@H]1[C@H]([C@H](C=CO1)OC(=O)C2=CC=CC=C2)O

Technology Process of L-arabino-Hex-5-enitol, 2,6-anhydro-1,5-dideoxy-, 4-benzoate

There total 2 articles about L-arabino-Hex-5-enitol, 2,6-anhydro-1,5-dideoxy-, 4-benzoate 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: 78.0%

benzoyl chloride (98-88-4) + L-fucal (80483-16-5) → Benzoic acid (2S,3S,4S)-4-hydroxy-2-methyl-3,4-dihydro-2H-pyran-3-yl ester (91861-12-0,104069-01-4,127000-08-2,130061-17-5) + 1,5-anhydro-3-O-benzoyl-2,6-dideoxy-L-lyxo-hex-1-enitol (130061-11-9) + dibenzoyl fucal (130061-16-4)

Guidance literature:

With triethylamine; In dichloromethane; for 4h; Ambient temperature;

DOI:10.1021/ja00180a037

Reference yield:

3,4-di-O-acetyl-L-fucal (54621-94-2) → 1,5-anhydro-3-O-benzoyl-2,6-dideoxy-L-lyxo-hex-1-enitol (130061-11-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / potassium carbonate / methanol / 3 h / Ambient temperature

2: 78 percent / triethylamine / CH₂Cl₂ / 4 h / Ambient temperature

With potassium carbonate; triethylamine; In methanol; dichloromethane;

DOI:10.1021/ja00180a037

Reference yield:

1,5-anhydro-3-O-benzoyl-2,6-dideoxy-L-lyxo-hex-1-enitol (130061-11-9) → 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)

Guidance literature:

Multi-step reaction with 5 steps

1: 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

2: 57 percent / triphenyltin hydride, azobis(isobutyronitrile) / benzene / 0.5 h / Heating

3: 75 percent / lithium aluminum hydride / tetrahydrofuran; diethyl ether / 0.5 h / 0 °C

4: 80 percent / imidazole / CH₂Cl₂ / 29 h / Heating

5: 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

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

DOI:10.1021/ja00180a037

upstream raw materials:

benzoyl chloride

L-fucal

3,4-di-O-acetyl-L-fucal

Downstream raw materials:

Benzoic acid (2S,3R,4S)-3-((2S,3R,5R,6S)-5-benzyloxy-3-iodo-6-methyl-tetrahydro-pyran-2-yloxy)-2-methyl-3,4-dihydro-2H-pyran-4-yl ester

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

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

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