(2S,3R,4S,5R)-2-Benzyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ol

Base Information

• Chemical Name: (2S,3R,4S,5R)-2-Benzyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ol
• CAS No.: 153751-47-4
• Molecular Formula: C₃₃H₃₄O₅
• Molecular Weight: 510.63
• Mol file: 153751-47-4.mol

Synonyms:(2S,3R,4S,5R)-2-Benzyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ol

Chemical Property of (2S,3R,4S,5R)-2-Benzyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S,5R)-2-Benzyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ol

There total 2 articles about (2S,3R,4S,5R)-2-Benzyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ol 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%

benzyllithium (766-04-1) + 2,3,4-tri-O-benzyl-D-xylono-1,5-lactone (153751-46-3) → (2S,3R,4S,5R)-2-Benzyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ol (153751-47-4)

Guidance literature:

In toluene; at -78 ℃; for 0.75h;

DOI:10.1021/jo00083a013

Reference yield:

2,3,4-tri-O-benzyl-D-xylopyranose (18039-26-4,20787-16-0,20787-21-7,77943-32-9,77943-33-0,89615-43-0,89615-44-1,90899-55-1) → (2S,3R,4S,5R)-2-Benzyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ol (153751-47-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / pyridinium chlorochromate / CH₂Cl₂ / 4 h / Ambient temperature

2: 75 percent / toluene / 0.75 h / -78 °C

With pyridinium chlorochromate; In dichloromethane; toluene;

DOI:10.1021/jo00083a013

Reference yield:

(2S,3R,4S,5R)-2-Benzyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ol (153751-47-4) → (2S,3R,4S,5R,6R)-2-((3R,4R,5R,6S)-6-Benzyl-4,5-dihydroxy-tetrahydro-pyran-3-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

Guidance literature:

Multi-step reaction with 4 steps

1: BF₃*OEt₂ / CH₂Cl₂ / 1 h / 0 °C

2: n-Bu₃SnH, AIBN / toluene / 3 h / 110 °C

3: 80 percent / H₂ / 10percent Pd/C / methanol / 96 h

4: H2O / Ambient temperature; β-galactosidase from E. coli, buffer (0.05 M Na phosphate, 1 mM MgCl2, 5 mM mercaptoethanol, pH 7.0)

With 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; hydrogen; tri-n-butyl-tin hydride; palladium on activated charcoal; In methanol; dichloromethane; water; toluene;

DOI:10.1021/jo00083a013

upstream raw materials:

benzyllithium

2,3,4-tri-O-benzyl-D-xylono-1,5-lactone

2,3,4-tri-O-benzyl-D-xylopyranose

Downstream raw materials:

(2R,3R,4S,5R)-2-Benzyl-3,4,5-tris-benzyloxy-2-phenylsulfanyl-tetrahydro-pyran