Ethyl 2-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyacetate

Base Information

• Chemical Name: Ethyl 2-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyacetate
• CAS No.: 103795-12-6
• Molecular Formula: C14H18 O4
• Molecular Weight: 250.295
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID70555153
• Mol file: 103795-12-6.mol

Synonyms:103795-12-6;ethyl 2-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyacetate;(2,2-DIMETHYL-[1,3]DIOXOLAN-4-YL)-HYDROXY-ACETIC ACID ETHYL ESTER;DTXSID70555153;AKOS015965637;Ethyl (2,2-dimethyl-1,3-dioxolan-4-yl)(hydroxy)acetate

Chemical Property of Ethyl 2-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyacetate

Chemical Property:

• Vapor Pressure: 0.000666mmHg at 25°C
• Refractive Index: 1.451
• Boiling Point: 274.8°C at 760 mmHg
• Flash Point: 101.4°C
• PSA: 64.99000
• Density: 1.142g/cm³
• LogP: 0.06190
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 204.09977361
• Heavy Atom Count: 14
• Complexity: 213

Purity/Quality:

99%min ^*data from raw suppliers

(2,2-DIMETHYL-(1,3)DIOXOLAN-4-YL)-HYDROXY-ACETIC ACID ETHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(C1COC(O1)(C)C)O

Technology Process of Ethyl 2-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyacetate

There total 31 articles about Ethyl 2-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyacetate 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: 100.0%

S(R)-1-deoxy-1-(p-tolylsulfinyl)-2-O-(benzyl)-3,4-O-isopropylidene-D-erythritol (274905-44-1) → (R)-2-(benzyloxy)-2-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde (103795-12-6)

Guidance literature:

With 2,6-dimethylpyridine; trifluoroacetic anhydride; In acetonitrile; at 20 ℃; for 3h;

DOI:10.1016/S0957-4166(00)00005-7

Reference yield: 100.0%

2-O-benzyl-3,4-O-isopropylidene-D-erythrose diethyldithioacetal → (R)-2-(benzyloxy)-2-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde (103795-12-6)

Guidance literature:

With water; mercury dichloride; mercury(II) oxide; In acetone; Ambient temperature;

DOI:10.1016/S0957-4166(99)00072-5

Reference yield: 97.0%

ethyl (R)-2-(benzyloxy)-2-[(4'R)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]acetate (287119-15-7) → (R)-2-(benzyloxy)-2-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde (103795-12-6)

Guidance literature:

With diisobutylaluminium hydride; In toluene; at -78 ℃; for 0.25h;

DOI:10.1002/1099-0690(200111)2001:21<4111::AID-EJOC4111>3.0.CO;2-7

upstream raw materials:

(+)-(3S,4R)-3-benzyloxy-4,5-O-isopropylidene-4,5-dihydroxy-1-pentene

(1R)-1-O-benzyl-2,3-O-isopropylidene-1-(2-thiazolyl)-D-glycitol

2-[(R)-Benzyloxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-3-methyl-thiazolidine

1-O-benzyl-3,4-O-isopropylidene-D-erythritol ⁽¹²⁾ and 2-O-benzyl-3,4-O-isopropylidene-D-erythritol

Downstream raw materials:

(3R,4S)-4-Benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-1-thiazol-2-yl-butan-1-one

(3S,4R,5R)-4-O-Benzyl-5,6-O-isopropylidene-3,4,5,6-tetrahydroxy-1-(2-thiazolyl)-1-hexanone

(1S,2R,3R)-2-O-benzyl-3,4-O-isopropylidene-1-(2-thiazolyl)-1,2,3,4-butanetetraol

(1R)-2-O-benzyl-3,4-O-isopropylidene-1-(2-thiazolyl)-D-erythritol

Refernces

• 1、 Kusakabe, Masato,Sato, Fumie. "Stereoselective Synthesis of D-Erythrose and D-Threose Derivatives from D-Glyceraldehyde Acetonide and their Reactions with 1-(Trimethylsilyl)vinyl Cuprate Reagent. Synthesis of Allitol Hexaacetate". . p. 1473 - 1476. Retrieved 1986.
• 2、 Arroyo-Gomez,Lopez-Sastre,Rodriguez-Amo,Santos-Garcia,Sanz-Tejedor. "Stereoselective preparation of O-alkoxy D-tetrose, D-pentose, 2-deoxy- D-glycero tetrose and 2,3-dideoxy-D-erythro pentose derivatives by an iterative elongation of 2,3-O-isopropylidene-D-glyceraldehyde". . p. 973 - 990. Retrieved 1999.
• 3、 Fernandez,Martin-Zamora,Pareja,Lassaletta. "Stereoselective nucleophilic formylation and cyanation of α-alkoxy- and α-aminoaldehydes". . p. 5201 - 5207. Retrieved 2007/10/03.