5-O-[(tert-Butyl)dimethylsilyl]-2,3-O-(1-methylethylidene)-L-lyxonic acid gamma-lactone

Base Information

• Chemical Name: 5-O-[(tert-Butyl)dimethylsilyl]-2,3-O-(1-methylethylidene)-L-lyxonic acid gamma-lactone
• CAS No.: 1044813-00-4
• Molecular Formula: C14H26O5Si
• Molecular Weight: 302.43874
• Mol file: 1044813-00-4.mol

Synonyms:5-O-[(tert-Butyl)dimethylsilyl]-2,3-O-(1-methylethylidene)-L-lyxonic acid gamma-lactone;5-O-[(dimethylethyl)dimethylsilyl]-2,3-O-Isopropyllidine-L-lyxoniacidr-lactone

Chemical Property of 5-O-[(tert-Butyl)dimethylsilyl]-2,3-O-(1-methylethylidene)-L-lyxonic acid gamma-lactone

Chemical Property:

• Boiling Point: 371.0±42.0 °C(Predicted)
• PSA: 53.99000
• Density: 1.031
• LogP: 2.45370

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-O-[(tert-Butyl)dimethylsilyl]-2,3-O-(1-methylethylidene)-L-lyxonic acid gamma-lactone

There total 5 articles about 5-O-[(tert-Butyl)dimethylsilyl]-2,3-O-(1-methylethylidene)-L-lyxonic acid gamma-lactone 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: 97.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 2,3-O-isopropylidene-L-lyxono-1,4-lactone (152006-17-2) → 5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-L-lyxonic acid-1,4-lactone (1044813-00-4)

Guidance literature:

With pyridine; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1002/ejoc.201301705

Reference yield:

(3R,4R,5R)-4,5-dihydro-3,4-(O,O)-isopropylidene-5-mesyloxymethyl-2-(3H)-furanone (89747-54-6) → 5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-L-lyxonic acid-1,4-lactone (1044813-00-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium hydroxide / water / 3 h / 20 °C / Large scale

2.1: dmap; 1H-imidazole / N,N-dimethyl-formamide / 1 h / Large scale

2.2: 16 h / 0 - 20 °C / Inert atmosphere; Large scale

With 1H-imidazole; dmap; potassium hydroxide; In water; N,N-dimethyl-formamide;

Reference yield:

D-Ribono-1,4-lactone (5336-08-3) → 5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-L-lyxonic acid-1,4-lactone (1044813-00-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 1 h / 20 °C / Large scale

1.2: 10 °C / Large scale

2.1: pyridine / 4 h / -15 - 20 °C / Inert atmosphere; Large scale

3.1: potassium hydroxide / water / 3 h / 20 °C / Large scale

4.1: dmap; 1H-imidazole / N,N-dimethyl-formamide / 1 h / Large scale

4.2: 16 h / 0 - 20 °C / Inert atmosphere; Large scale

With pyridine; 1H-imidazole; dmap; potassium hydroxide; In water; N,N-dimethyl-formamide;

upstream raw materials:

tert-butyldimethylsilyl chloride

2,3-O-isopropylidene-L-lyxono-1,4-lactone

(3R,4R,5R)-4,5-dihydro-3,4-(O,O)-isopropylidene-5-mesyloxymethyl-2-(3H)-furanone

D-Ribose

Downstream raw materials:

1-amino-1,4-anhydro-N-benzyl-5-O-tertbutyldimethylsilyl-1-deoxy-2,3-O-isopropylidene-D-ribitol

(3aR,4R,6aS)-4-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)tetrahydro-2,2-dimethyl-3aH-[1,3]dioxolo[4,5-c]pyrrole

(3aR,4R,6aS)-4-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-4,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole

1S-5-O-tert-butyldimethylsilyl-1,4-dideoxy-1-C-[(4-methyoxypyrrolo[3,2-d]pyrimidin-9-N-(benzyloxomethyl)-7-yl)]-1,4-imino-2,3-O-isopropylidine-D-ribitol

Refernces

• 1、 Ayers, Benjamin J.,Fleet, George W.J.. "One-pot tandem strecker reaction and iminocyclisations: Syntheses of trihydroxypiperidine α-iminonitriles". . p. 2053 - 2069. Retrieved 2014/04/17.
• 2、 -. "RIBONUCLEIC ACIDs WITH 4'-THIO-MODIFIED NUCLEOTIDES AND RELATED METHODS". Paragraph 0134. . Retrieved 2014/10/04.