(S)-(2,2-Dimethyl-1,3-dioxan-4-yl)methanol

Base Information

• Chemical Name: (S)-(2,2-Dimethyl-1,3-dioxan-4-yl)methanol
• CAS No.: 85287-64-5
• Molecular Formula: C7H14O3
• Molecular Weight: 146.186
• Hs Code.: 2940000080
• DSSTox Substance ID: DTXSID60509625
• Wikidata: Q72469820
• Mol file: 85287-64-5.mol

Synonyms:(S)-(2,2-Dimethyl-1,3-dioxan-4-yl)methanol;85287-64-5;[(4S)-2,2-Dimethyl-1,3-dioxan-4-yl]methanol;SCHEMBL13305484;DTXSID60509625;AKOS016014509;CS-0312029;A917561

Chemical Property of (S)-(2,2-Dimethyl-1,3-dioxan-4-yl)methanol

Chemical Property:

• PSA: 38.69000
• Density: 1.004
• LogP: 0.52030
• Storage Temp.: 2-8°C
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 146.094294304
• Heavy Atom Count: 10
• Complexity: 111

Purity/Quality:

98%Min ^*data from raw suppliers

(S)-(2,2-Dimethyl-1,3-dioxan-4-yl)methanol 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OCCC(O1)CO)C
• Isomeric SMILES: CC1(OCC[C@H](O1)CO)C

Technology Process of (S)-(2,2-Dimethyl-1,3-dioxan-4-yl)methanol

There total 12 articles about (S)-(2,2-Dimethyl-1,3-dioxan-4-yl)methanol 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: 82.0%

ethyl (S)-2,4-dihydroxybutanoate 2,4-acetonide (94339-92-1) → (S)-butane-1,2,4-triol 2,4-acetonide (85287-64-5)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether;

DOI:10.1016/S0040-4039(01)91192-X

Reference yield: 10.0%

2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol (32233-43-5) → (S)-butane-1,2,4-triol 2,4-acetonide (85287-64-5)

Guidance literature:

With boron trifluoride diethyl etherate; In chloroform; at 25 ℃; for 3h;

DOI:10.1016/S0040-4039(00)85738-X

Reference yield:

(S)-diethyl malate 2-(1-methyl-1-methoxyethyl ether) (66348-32-1) → (S)-butane-1,2,4-triol 2,4-acetonide (85287-64-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / LiAlH₄ / tetrahydrofuran / 5 h / Ambient temperature

2: BF₃*Et₂O / diethyl ether / 3 h / Ambient temperature

With lithium aluminium tetrahydride; boron trifluoride diethyl etherate; In tetrahydrofuran; diethyl ether;

DOI:10.1021/jo00376a011

upstream raw materials:

(S)-1,2,4-butanetriol 2-(1-methyl-1-methoxyethyl ether)

ethyl (S)-2,4-dihydroxybutanoate 2,4-acetonide

2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol

(S)-1,2,4-butanetriol

Downstream raw materials:

(S)-butane-1,2,4-triol 2,4-acetonide 1-tosylate

(4S)-4-(2-[(4-methoxybenzyl)oxy]ethyl)-2,2-dimethyl-1,3-dioxolane

(R)-1,7-dioxaspiro[5.5]undecane

(R)-(-)-1,7-dioxaspiro<5.5>undecane

Refernces

• 1、 Meyers,Lawson,Walker,Linderman. "Synthetic studies on the streptogramin antibiotics. Enantioselective synthesis of the oxazole dienyl amine moiety". . p. 5111 - 5123. Retrieved 2007/10/02.
• 2、 Mori, Kenji,Uematsu, Tamon,Watanabe, Hidenori,Yanagi, Kazunori,Minobe, Masao. "SYNTHESIS OF THE ENANTIOMERS OF 1,7-DIOXASPIROUNDECANE AND 4-HYDROXY 1,7-DIOXASPIROUNDECANE, THE COMPONENTS OF THE OLIVE FLY PHEROMONE". . p. 3875 - 3878. Retrieved 2007/10/02.