(-)-Varitriol

Base Information

• Chemical Name: (-)-Varitriol
• CAS No.: 906482-48-2
• Molecular Formula: C15H20O5
• Molecular Weight: 280.321
• DSSTox Substance ID: DTXSID30468452
• Nikkaji Number: J2.349.061G
• Wikidata: Q75066945
• Mol file: 906482-48-2.mol

Synonyms:(-)-Varitriol;906482-48-2;(2S,3R,4S,5R)-2-[(E)-2-[2-(hydroxymethyl)-3-methoxyphenyl]ethenyl]-5-methyloxolane-3,4-diol;DTXSID30468452;CHEBI:199545;(2S,3R,4S,5R)-2-((E)-2-(Hydroxymethyl)-3-methoxystyryl)-5-methyltetrahydrofuran-3,4-diol

Chemical Property of (-)-Varitriol

Chemical Property:

• PSA: 79.15000
• LogP: 0.70980
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 280.13107373
• Heavy Atom Count: 20
• Complexity: 332

Purity/Quality:

95% ^*data from raw suppliers

(-)-Varitriol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C(O1)C=CC2=C(C(=CC=C2)OC)CO)O)O
• Isomeric SMILES: C[C@@H]1[C@H]([C@H]([C@@H](O1)/C=C/C2=C(C(=CC=C2)OC)CO)O)O

Technology Process of (-)-Varitriol

There total 5 articles about (-)-Varitriol 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: 75.0%

2-[(E)-2-(2-tert-butyldimethylsilyloxymethyl-3-methoxyphenyl)styryl]-4',5'-O-isopropylidene-7'-deoxy-D-ribofuranose (906102-77-0) → (2S,3R,4S,5R,E)-2-(2-(hydroxymethyl)-3-methoxystyryl)-5-methyltetrahydrofuran-3,4-diol (906482-48-2)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1039/b603931f

Reference yield: 67.0%

tri-O-acetylvaritriol → (2S,3R,4S,5R,E)-2-(2-(hydroxymethyl)-3-methoxystyryl)-5-methyltetrahydrofuran-3,4-diol (906482-48-2)

Guidance literature:

Saponification;

DOI:10.1016/j.tet.2007.09.057

Reference yield:

methyl 2-((E)-2-((3aS,4S,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)vinyl)-6-methoxybenzoate (1415904-94-7) → (2S,3R,4S,5R,E)-2-(2-(hydroxymethyl)-3-methoxystyryl)-5-methyltetrahydrofuran-3,4-diol (906482-48-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 2.25 h / 0 - 20 °C

2: lithium triethylborohydride / tetrahydrofuran / 0.17 h / -78 °C

3: hydrogenchloride / tetrahydrofuran; water / 3 h / 20 °C

With 1H-imidazole; hydrogenchloride; iodine; lithium triethylborohydride; triphenylphosphine; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/j.tetasy.2012.10.010

upstream raw materials:

2-[(E)-2-(2-tert-butyldimethylsilyloxymethyl-3-methoxyphenyl)styryl]-4',5'-O-isopropylidene-7'-deoxy-D-ribofuranose

methyl 2-((E)-2-((3aS,4S,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)vinyl)-6-methoxybenzoate

methyl 2-((E)-2-((3aS,4S,6S,6aS)-6-(iodomethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)vinyl)-6-methoxybenzoate