1-[(4S,5R)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanone

Base Information

• Chemical Name: 1-[(4S,5R)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanone
• CAS No.: 144829-98-1
• Molecular Formula: C8H14 O3
• Molecular Weight: 158.2
• DSSTox Substance ID: DTXSID801194787
• Mol file: 144829-98-1.mol

Synonyms:144829-98-1;1-[(4S,5R)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanone;D-threo-2-Pentulose, 1,5-dideoxy-3,4-O-(1-methylethylidene)- (9CI);DECGIDYVUDWJEE-RNFRBKRXSA-N;DTXSID801194787;1,5-Dideoxy-3,4-O-(1-methylethylidene)-D-threo-2-pentulose

Chemical Property of 1-[(4S,5R)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanone

Chemical Property:

• PSA: 35.53000
• LogP: 1.11540
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 158.094294304
• Heavy Atom Count: 11
• Complexity: 174

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(OC(O1)(C)C)C(=O)C
• Isomeric SMILES: C[C@@H]1[C@H](OC(O1)(C)C)C(=O)C

Technology Process of 1-[(4S,5R)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanone

There total 13 articles about 1-[(4S,5R)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanone 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: 84.0%

(2RS,3R,4R)-3,4-(isopropylidenedioxy)-2-pentanol → (3S,4R)-3,4-(isopropylidenedioxy)-2-propanone (144829-98-1)

Guidance literature:

With silica gel; pyridinium chlorochromate; In dichloromethane; for 20h; Ambient temperature;

Reference yield: 79.0%

(4R,5S)-N-methoxy-N,2,2,5-tetramethyl-1,3-dioxolane-4-carboxamide (1336854-12-6) + methylmagnesium chloride (676-58-4) → 1-((4R,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl)ethanone (81703-36-8,57671-97-3,81703-33-5,144829-98-1)

Guidance literature:

In tetrahydrofuran; at 0 ℃; Inert atmosphere;

DOI:10.1021/jo2016746

Reference yield: 75.0%

methylmagnesium bromide (75-16-1) + (4S,5R)-2,2,5-Trimethyl-[1,3]dioxolane-4-carboxylic acid methoxy-methyl-amide → (3S,4R)-3,4-(isopropylidenedioxy)-2-propanone (144829-98-1)

Guidance literature:

In tetrahydrofuran; at -10 ℃;

DOI:10.1016/S0040-4039(00)61535-6

upstream raw materials:

1-((4S,5S)-2,2,5-Trimethyl-[1,3]dioxolan-4-yl)-ethanol

(4R,5S)-2,2,5-trimethyl-1,3-dioxolane-4-carbaldehyde

biphenyl-4-ylmethyl (4R,5S)-2,2,5-trimethyl-1,3-dioxolane-4-carboxylate

(4R,5S)-N-methoxy-N,2,2,5-tetramethyl-1,3-dioxolane-4-carboxamide

Downstream raw materials:

(2S)-2-<(R)-1-(benzyloxy)-1-<(tert-butyldimethylsiloxy)methyl>ethyl>-N-<(2E,6E)-(4R,8R,9R)-8,9-(isopropylidenedioxy)-4,7-dimethyl-2,6-decadien-1-yl>pyrrolidine

(2S)-2-<(R)-1-(benzyloxy)-1-formylethyl>-N-<(2E,6E)-(4R,8R,9R)-8,9-(isopropylidenedioxy)-4,7-dimethyl-2,6-decadien-1-yl>pyrrolidine

(2S)-2-<(R)-1-(benzyloxy)-1-(hydroxymethyl)ethyl>-N-<(2E,6E)-(4R,8R,9R)-8,9-(isopropylidenedioxy)-4,7-dimethyl-2,6-decadien-1-yl>pyrrolidine

(7R,8R,8aS)-8-(benzyloxy)-7-hydroxy-6(Z)-<6(R),7(R)-(isopropylidenedioxy)-2(R),5-dimethyl-4(E)-octenylidene>-8-methyloctahydroindolizine

Refernces

• 1、 Smaltz, Daniel J.,Myers, Andrew G.. "Scalable synthesis of enantiomerically pure syn -2,3-dihydroxybutyrate by sharpless asymmetric dihydroxylation of p -phenylbenzyl crotonate". . p. 8554 - 8559. Retrieved 2011/12/03.
• 2、 Ziegler, Frederick E.,Kim, Hakwon. "A Selective Baeyer-Villiger Oxidation: A Total Synthesis of (-)-Acetomycin". . p. 7669 - 7672. Retrieved 2007/10/02.