(2R,3S,4R)-4-phenylmethoxy-2-(phenylmethoxymethyl)-3,4-dihydro-2H-pyran-3-ol

Base Information

• Chemical Name: (2R,3S,4R)-4-phenylmethoxy-2-(phenylmethoxymethyl)-3,4-dihydro-2H-pyran-3-ol
• CAS No.: 145852-76-2
• Molecular Formula: C20H22 O4
• Molecular Weight: 326.392
• DSSTox Substance ID: DTXSID40370476
• Nikkaji Number: J1.082.427C,J1.333.272J
• Wikidata: Q82157634
• Mol file: 145852-76-2.mol

Synonyms:145852-76-2;(2R,3S,4R)-4-phenylmethoxy-2-(phenylmethoxymethyl)-3,4-dihydro-2H-pyran-3-ol;ST50405673;SCHEMBL5162509;DTXSID40370476;1,2-Dideoxy-3-O,6-O-dibenzyl-D-arabino-1-hexenopyranose;3-O,6-O-Dibenzyl-1,2-didehydro-1,2-dideoxy-D-glucopyranose;(2R,3S,4R)-4-(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyran-3-ol

Chemical Property of (2R,3S,4R)-4-phenylmethoxy-2-(phenylmethoxymethyl)-3,4-dihydro-2H-pyran-3-ol

Chemical Property:

• Vapor Pressure: 4.84E-10mmHg at 25°C
• Boiling Point: 480.5°Cat760mmHg
• Flash Point: 244.4°C
• Density: 1.19g/cm³
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 326.15180918
• Heavy Atom Count: 24
• Complexity: 372

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Safety Statements: S24/25:Avoid contact with skin and eyes.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COCC2C(C(C=CO2)OCC3=CC=CC=C3)O
• Isomeric SMILES: C1=CC=C(C=C1)COC[C@@H]2[C@H]([C@@H](C=CO2)OCC3=CC=CC=C3)O

Technology Process of (2R,3S,4R)-4-phenylmethoxy-2-(phenylmethoxymethyl)-3,4-dihydro-2H-pyran-3-ol

There total 16 articles about (2R,3S,4R)-4-phenylmethoxy-2-(phenylmethoxymethyl)-3,4-dihydro-2H-pyran-3-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: 78.0%

(2R,3S,4R)-4-Benzyloxy-2-benzyloxymethyl-3-(4-methoxy-benzyloxy)-3,4-dihydro-2H-pyran (913258-73-8) → 3,6-di-O-benzyl-D-glucal (145852-76-2)

Guidance literature:

With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; tert-butyl alcohol; at 0 - 20 ℃; for 3h; pH=7; aq. phosphate buffer;

DOI:10.1021/jo102382r

Reference yield: 25.0%

benzyl bromide (100-39-0) + D-glucal (13265-84-4) → 3,4,6-tri-O-benzyl-D-glucal (55628-54-1) + 3,6-di-O-benzyl-D-glucal (145852-76-2) + 1,5-Anhydro-4,6-di-O-benzyl-2-deoxy-D-arabino-hex-1-enitol (203630-08-4)

Guidance literature:

D-glucal; With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h;

benzyl bromide; In N,N-dimethyl-formamide; at 20 ℃; for 24h;

DOI:10.1016/S0960-894X(02)00471-7

Reference yield:

D-glucal triacetate (2873-29-2) → 3,6-di-O-benzyl-D-glucal (145852-76-2)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOMe / methanol / 5 h / Ambient temperature

2: 1.) (Bu₃Sn)2O, 2.) TBABr / 1.) benzene, reflux, 20 h, 2.) benzene, reflux, 17 h

With tetrabutylammomium bromide; sodium methylate; bis(tri-n-butyltin)oxide; In methanol;

DOI:10.1021/ja962048b

upstream raw materials:

benzyl bromide

D-glucal

D-glucal triacetate

(4aR,8R,8aS)-2-(4-methoxyphenyl)-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxin-8-ol

Downstream raw materials:

1,5-anhydro-4-O-tert-butyldimethylsilyl-2-deoxy-3,6-di-O-benzyl-D-arabino-hex-1-enitol

3,6-di-O-benzyl-4-deoxy-D-glucal

methyl 3,6-di-O-benzyl-4-deoxy-1R-D-galactopyranose

C₂₀H₂₂O₄

Refernces

• 1、 Alberch, Laura,Cheng, Gang,Seo, Seung-Kee,Li, Xuehua,Boulineau, Fabien P.,Wei, Alexander. "Stereoelectronic factors in the stereoselective epoxidation of glycals and 4-deoxypentenosides". . p. 2532 - 2547. Retrieved 2011/06/19.
• 2、 Boulineau, Fabien P.,Wei, Alexander. "Conversion of D-Glucals into L-Glycals and Mirror-Image Carbohydrates". . p. 119 - 121. Retrieved 2007/10/03.