Xylofuranose, benzyl isopropylidene, toluenesulf

Base Information

• Chemical Name: Xylofuranose, benzyl isopropylidene, toluenesulf
• CAS No.: 29581-48-4
• Molecular Formula: C22H26 O7 S
• Molecular Weight: 434.51
• DSSTox Substance ID: DTXSID90952064
• Mol file: 29581-48-4.mol

Synonyms:29581-48-4;Xylofuranose, benzyl isopropylidene, toluenesulf;DTXSID90952064;3-O-Benzyl-5-O-(4-methylbenzene-1-sulfonyl)-1,2-O-(1-methylethylidene)pentofuranose

Chemical Property of Xylofuranose, benzyl isopropylidene, toluenesulf

Chemical Property:

• Vapor Pressure: 9.86E-12mmHg at 25°C
• Boiling Point: 553.6°Cat760mmHg
• Flash Point: 288.6°C
• PSA: 88.67000
• Density: 1.32g/cm³
• LogP: 4.24290
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 434.13992434
• Heavy Atom Count: 30
• Complexity: 660

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OCC2C(C3C(O2)OC(O3)(C)C)OCC4=CC=CC=C4
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)OC[C@@H]2[C@@H]([C@@H]3C(O2)OC(O3)(C)C)OCC4=CC=CC=C4

Technology Process of Xylofuranose, benzyl isopropylidene, toluenesulf

There total 16 articles about Xylofuranose, benzyl isopropylidene, toluenesulf 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: 99.4%

3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose (34370-91-7,59358-33-7,68354-70-1,70798-12-8,19139-80-1) + p-toluenesulfonyl chloride (98-59-9) → O-benzyl-1,2-di-O-isopropylidene-5-O-(p-toluenesulfonyl)-α-D-xylofuranose (29581-48-4)

Guidance literature:

With pyridine; at 60 ℃;

DOI:10.1016/S0008-6215(98)00135-9

Reference yield: 95.0%

benzyl bromide (100-39-0) + 1,2-di-O-isopropylidene-5-O-tosyl-D-xylofuranose (6893-65-8,20513-95-5,20513-96-6,34981-06-1,40429-51-4,110349-61-6) → O-benzyl-1,2-di-O-isopropylidene-5-O-(p-toluenesulfonyl)-α-D-xylofuranose (29581-48-4)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; paraffin oil; at 0 ℃; for 1h;

DOI:10.1021/acs.joc.5b02894

Reference yield:

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose (23558-05-6) → O-benzyl-1,2-di-O-isopropylidene-5-O-(p-toluenesulfonyl)-α-D-xylofuranose (29581-48-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / NaBH₄ / methanol / 2 h / 0 °C

2: 93 percent / pyridine; DMAP / CH₂Cl₂ / 5 h

With pyridine; dmap; sodium tetrahydroborate; In methanol; dichloromethane;

DOI:10.1016/j.tetlet.2006.11.048

upstream raw materials:

3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose

p-toluenesulfonyl chloride

benzyl bromide

1,2-di-O-isopropylidene-5-O-tosyl-D-xylofuranose

Downstream raw materials:

3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose

2,5-anhydro-3-O-benzyl-D-xylose diethyl acetal

4-benzyloxy-5-dimethoxymethyl-tetrahydro-furan-3-ol

(2R,3S,4R)-3-(benzyloxy)-4-hydroxytetrahydrofuran-2-carbaldehyde