L-threo-2-Pentulose, 1,5-dideoxy-3,4-O-(1-methylethylidene)- (9CI)

Base Information

• Chemical Name: L-threo-2-Pentulose, 1,5-dideoxy-3,4-O-(1-methylethylidene)- (9CI)
• CAS No.: 81703-36-8
• Molecular Formula: C₈H₁₄O₃
• Molecular Weight: 158.197
• Mol file: 81703-36-8.mol

Synonyms:L-threo-2-Pentulose, 1,5-dideoxy-3,4-O-(1-methylethylidene)- (9CI)

Chemical Property of L-threo-2-Pentulose, 1,5-dideoxy-3,4-O-(1-methylethylidene)- (9CI)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of L-threo-2-Pentulose, 1,5-dideoxy-3,4-O-(1-methylethylidene)- (9CI)

There total 5 articles about L-threo-2-Pentulose, 1,5-dideoxy-3,4-O-(1-methylethylidene)- (9CI) 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: 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:

biphenyl-4-ylmethyl (4R,5S)-2,2,5-trimethyl-1,3-dioxolane-4-carboxylate (1336854-09-1) → 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:

Multi-step reaction with 3 steps

1: lithium hydroxide / tetrahydrofuran; methanol; water / 0.25 h / 0 °C / Inert atmosphere

2: 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 3.5 h / -20 °C / Inert atmosphere

3: tetrahydrofuran / 0 °C / Inert atmosphere

With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1021/jo2016746

Reference yield:

(4R,5S)-2,2,5-trimethyl-1,3-dioxolane-4-carboxylic acid (107983-40-4,152786-08-8,92741-26-9) → 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:

Multi-step reaction with 2 steps

1: 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 3.5 h / -20 °C / Inert atmosphere

2: tetrahydrofuran / 0 °C / Inert atmosphere

With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo2016746

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