1,7-Dioxaspiro[4.4]nonan-8-one, 3,4-bis(phenylmethoxy)-, (3R,4S,5R)-

Base Information

• Chemical Name: 1,7-Dioxaspiro[4.4]nonan-8-one, 3,4-bis(phenylmethoxy)-, (3R,4S,5R)-
• CAS No.: 189328-24-3
• Molecular Formula: C21H22O5
• Molecular Weight: 354.403
• DSSTox Substance ID: DTXSID60451074
• Nikkaji Number: J820.250H
• Wikidata: Q82270941
• Mol file: 189328-24-3.mol

Synonyms:1,7-Dioxaspiro[4.4]nonan-8-one, 3,4-bis(phenylmethoxy)-, (3R,4S,5R)-;189328-24-3;DTXSID60451074;(5R)-3beta,4alpha-Bis(benzyloxy)-1,7-dioxaspiro[4.4]nonan-8-one

Chemical Property of 1,7-Dioxaspiro[4.4]nonan-8-one, 3,4-bis(phenylmethoxy)-, (3R,4S,5R)-

Chemical Property:

• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 354.14672380
• Heavy Atom Count: 26
• Complexity: 469

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C2(O1)CC(=O)OC2)OCC3=CC=CC=C3)OCC4=CC=CC=C4
• Isomeric SMILES: C1[C@H]([C@@H]([C@@]2(O1)CC(=O)OC2)OCC3=CC=CC=C3)OCC4=CC=CC=C4

Technology Process of 1,7-Dioxaspiro[4.4]nonan-8-one, 3,4-bis(phenylmethoxy)-, (3R,4S,5R)-

There total 23 articles about 1,7-Dioxaspiro[4.4]nonan-8-one, 3,4-bis(phenylmethoxy)-, (3R,4S,5R)- 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: 88.0%

3,4-bis(benzyloxy)-6-hydroxy-1,7-dioxaspiro[4.4]nonan-8-one (1353888-95-5) → 3,4-bis(benzyloxy)-1,7-dioxaspiro[4.4]nonan-8-one (189328-24-3)

Guidance literature:

With triethylsilane; trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 4h;

Reference yield: 72.0%

(R)-4-((1S,2R)-1,2-Bis-benzyloxy-3-hydroxy-propyl)-4-hydroxy-dihydro-furan-2-one (219566-68-4) → 3,4-bis(benzyloxy)-1,7-dioxaspiro[4.4]nonan-8-one (189328-24-3)

Guidance literature:

With dmap; triethylamine; p-toluenesulfonyl chloride; In dichloromethane; Ambient temperature;

DOI:10.1016/S0040-4039(98)01944-3

Reference yield:

(2R,3R)-2,3-bis(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)butan-1-ol (171622-74-5) → 3,4-bis(benzyloxy)-1,7-dioxaspiro[4.4]nonan-8-one (189328-24-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 2.) n-BuLi / 1.) Swern oxid., 2.) THF, -78 deg C

2: 90 percent / Swern oxid.

3: 94 percent / LHMDS / tetrahydrofuran / -78 °C

4: 95 percent / TBAF-HF

6: 78 percent / H₂ / Lindlar catalyst

7: O₃, pyridine / CH₂Cl₂

8: NaBH₄ / methanol

9: DBU / CH₂Cl₂

With pyridine; sodium tetrahydroborate; n-butyllithium; hydrogen fluoride; tetrabutyl ammonium fluoride; hydrogen; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium hexamethyldisilazane; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/S0040-4039(97)00380-8

upstream raw materials:

(R)-4-((1S,2R)-1,2-Bis-benzyloxy-3-hydroxy-propyl)-4-hydroxy-dihydro-furan-2-one

xylulose

benzyl bromide

1-(tert-butyl-diphenyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxymethyl)-hept-6-ene-2,3,4-triol