(4S,5R)-4-(hydroxymethyl)-2-phenyl-1,3-dioxan-5-ol

Base Information

• Chemical Name: (4S,5R)-4-(hydroxymethyl)-2-phenyl-1,3-dioxan-5-ol
• CAS No.: 81577-58-4
• Molecular Formula: C11H14O4
• Molecular Weight: 210.23
• European Community (EC) Number: 663-918-6
• Nikkaji Number: J1.366.108A

Synonyms:(4S,5R)-4-(hydroxymethyl)-2-phenyl-1,3-dioxan-5-ol;81577-58-4;starbld0048900;SCHEMBL756260

Chemical Property of (4S,5R)-4-(hydroxymethyl)-2-phenyl-1,3-dioxan-5-ol

Chemical Property:

• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 210.08920892
• Heavy Atom Count: 15
• Complexity: 191

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC(O1)C2=CC=CC=C2)CO)O
• Isomeric SMILES: C1[C@H]([C@@H](OC(O1)C2=CC=CC=C2)CO)O

Technology Process of (4S,5R)-4-(hydroxymethyl)-2-phenyl-1,3-dioxan-5-ol

There total 9 articles about (4S,5R)-4-(hydroxymethyl)-2-phenyl-1,3-dioxan-5-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: 87.0%

4,6-O-benzylidene-D-glucopyranose (30688-66-5,3006-41-5,20771-09-9,25152-90-3,97232-16-1,104022-77-7,113566-67-9,113566-68-0) → (4S,5R)-4-(hydroxymethyl)-2-phenyl-1,3-dioxan-5-ol (20638-61-3,81577-58-4,100023-68-5,117122-84-6)

Guidance literature:

4,6-O-benzylidene-D-glucopyranose; With sodium periodate; In methanol; water;

With sodium tetrahydroborate;

DOI:10.1002/ejoc.201500519

Reference yield: 70.0%

(4aR,7R,8R,8aR)-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-6,7,8-triol (3006-41-5) → 1,3-(R)-O-benzylidene-D-threitol (81577-58-4)

Guidance literature:

With sodium tetrahydroborate; sodium periodate; sodium hydrogencarbonate; In methanol; water; for 0.5h; pH=10;

DOI:10.1002/ejoc.200400557

Reference yield: 30.0%

(2R,4S,4aS,6S,8aR)-2-((2S,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-6-phenyl-tetrahydro-[1,3]dioxino[5,4-d][1,3]dioxin-4-ol (80995-79-5) → 1,3-(R)-O-benzylidene-D-threitol (81577-58-4)

Guidance literature:

With sodium hydride; methyl iodide; In tetrahydrofuran; for 2h;

upstream raw materials:

benzaldehyde dimethyl acetal

4,6-O-benzylidene-D-glucopyranose

(2R,4S,4aS,6S,8aR)-2-((2S,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-6-phenyl-tetrahydro-[1,3]dioxino[5,4-d][1,3]dioxin-4-ol

2,4-O-benzylidene-D-threose

Downstream raw materials:

(2R,3S)-2,4-bis(benzyloxy)butane-1,3-diol

1,3-O-benzylidene-D-threitol 4-(t-butyldimethylsilyl) ether

1,3-O-benzylidene-2-O-(but-2'-ynyl)-D-threitol

1,3-O-benzylidene-2-O-(but-2'-ynyl)-4-O-t-butyldimethylsilyl-D-threitol

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