[(2R,3R,4R)-3-Acetyloxy-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3,4-dihydro-2H-pyran-4-yl] acetate

Base Information

• Chemical Name: [(2R,3R,4R)-3-Acetyloxy-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3,4-dihydro-2H-pyran-4-yl] acetate
• CAS No.: 312692-93-6
• Molecular Formula: C₂₆H₃₂O₆Si
• Molecular Weight: 468.622
• DSSTox Substance ID: DTXSID70584084
• Wikidata: Q82475714
• Mol file: 312692-93-6.mol

Synonyms:312692-93-6;[(2R,3R,4R)-3-Acetyloxy-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3,4-dihydro-2H-pyran-4-yl] acetate;DTXSID70584084;3,4-Di-O-acetyl-6-O-(tert-butyldiphenylsilyl)-D-galactal, AldrichCPR;3,4-Di-O-acetyl-2,6-anhydro-1-O-[tert-butyl(diphenyl)silyl]-5-deoxy-D-arabino-hex-5-enitol

Chemical Property of [(2R,3R,4R)-3-Acetyloxy-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3,4-dihydro-2H-pyran-4-yl] acetate

Chemical Property:

• Refractive Index: n20/D 1.526(lit.)
• Flash Point: 150 °F
• PSA: 71.06000
• LogP: 3.33890
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 468.19681527
• Heavy Atom Count: 33
• Complexity: 669

Purity/Quality:

3,4-Di-O-acetyl-6-O-(tert-butyldiphenylsilyl)-D-galactal Aldrich ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)OC1C=COC(C1OC(=O)C)CO[Si](C2=CC=CC=C2)(C3=CC=CC=C3)C(C)(C)C
• Isomeric SMILES: CC(=O)O[C@@H]1C=CO[C@@H]([C@@H]1OC(=O)C)CO[Si](C2=CC=CC=C2)(C3=CC=CC=C3)C(C)(C)C

Technology Process of [(2R,3R,4R)-3-Acetyloxy-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3,4-dihydro-2H-pyran-4-yl] acetate

There total 10 articles about [(2R,3R,4R)-3-Acetyloxy-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3,4-dihydro-2H-pyran-4-yl] acetate 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: 95.0%

(2R,3S,4R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3,4-diol (87316-22-1) + acetic anhydride (108-24-7) → 3,4-di-O-acetyl-6-O-(tert-butyl diphenylsilyl)-D-glucal (151797-32-9,312692-93-6)

Guidance literature:

With pyridine; In dichloromethane;

DOI:10.1080/00397919308018600

Reference yield: 94.1%

1,5-anhydro-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-lyxo-hex-1-enitol (87316-22-1,137893-35-7) + acetic anhydride (108-24-7) → 3,4-di-O-acetyl-6-O-(tert-butyl diphenylsilyl)-D-galactal (312692-93-6)

Guidance literature:

With pyridine; In dichloromethane; Inert atmosphere;

Reference yield: 88.0%

2,3,4-tri-O-acetyl-6-O-[(1,1-dimethylethyl)diphenylsilyl]-α-D-glucopyranosyl bromide (180072-36-0) → 3,4-di-O-acetyl-6-O-(tert-butyl diphenylsilyl)-D-glucal (151797-32-9,312692-93-6)

Guidance literature:

With bis(cyclopentadienyl)-titanium(III) chloride; In tetrahydrofuran; Ambient temperature;

DOI:10.1016/0040-4039(96)00865-9

upstream raw materials:

(2R,3S,4R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3,4-diol

acetic anhydride

2,3,4-tri-O-acetyl-6-O-[(1,1-dimethylethyl)diphenylsilyl]-α-D-glucopyranosyl bromide

1,2,3,4-tetra-O-acetyl-D-glucopyranose

Refernces

• 1、 Spencer, Roxanne P.,Cavallaro, Cullen L.,Schwartz, Jeffrey. "Rapid preparation of variously protected glycals using titanium(III)". . p. 3987 - 3995. Retrieved 2007/10/03.
• 2、 Bouillot,Do Khac,Fetizon,Guir,Memoria. "Convenient preparations of 2,3-dihydro-4H-pyran-4-ones from D-glucal triacetate: Selective oxidations of allylic acetates and allylic silyl ethers using N-bromosuccinimide". . p. 2071 - 2081. Retrieved 2007/10/02.