D-erythro-Pent-4-enose, 4,5-dideoxy-2,3-O-(1-methylethylidene)- (9CI)

Base Information

• Chemical Name: D-erythro-Pent-4-enose, 4,5-dideoxy-2,3-O-(1-methylethylidene)- (9CI)
• CAS No.: 155934-55-7
• Molecular Formula: C8H12 O3
• Molecular Weight: 156.181
• Mol file: 155934-55-7.mol

Synonyms:D-erythro-Pent-4-enose, 4,5-dideoxy-2,3-O-(1-methylethylidene)- (9CI)

Chemical Property of D-erythro-Pent-4-enose, 4,5-dideoxy-2,3-O-(1-methylethylidene)- (9CI)

Chemical Property:

• Boiling Point: 212.8±40.0 °C(Predicted)
• PSA: 35.53000
• Density: 1.142±0.06 g/cm3(Predicted)
• LogP: 0.89140

Purity/Quality:

(4R,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolane-4-carbaldehyde >96% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of D-erythro-Pent-4-enose, 4,5-dideoxy-2,3-O-(1-methylethylidene)- (9CI)

There total 20 articles about D-erythro-Pent-4-enose, 4,5-dideoxy-2,3-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: 100.0%

methyl 5-deoxy-5-iodo-2,3-isopropylidene-β-D-ribofuranoside (38838-06-1) → (4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolane-4-carbaldehyde (155934-55-7)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -80 ℃; for 2h;

DOI:10.1515/znb-2006-0414

Reference yield: 85.0%

methyl 2,3-O-isopropylidene-D-ribofuranoside (4099-85-8,5531-21-5,20672-63-3,20672-65-5,58763-00-1,63029-07-2,72402-14-3,84894-45-1,129263-68-9,828937-29-7) → (4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolane-4-carbaldehyde (155934-55-7)

Guidance literature:

methyl 2,3-O-isopropylidene-D-ribofuranoside; With 1H-imidazole; iodine; triphenylphosphine; In toluene; Heating;

With zinc; In methanol; Heating;

DOI:10.1021/ol052106a

Reference yield: 83.0%

(3aS,4S,6aR)-4-(iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole (50600-40-3) → (4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolane-4-carbaldehyde (155934-55-7)

Guidance literature:

With zinc; In methanol; at 60 ℃; for 0.333333h; Inert atmosphere; Large scale;

DOI:10.1021/acs.jmedchem.6b00689

upstream raw materials:

methyl 5-deoxy-5-iodo-2,3-isopropylidene-β-D-ribofuranoside

(3aS,4S,6aR)-4-(iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole

(4S,5R)-2,2-dimethyl-4-hydroxymethyl-5-vinyl-1,3-dioxolane

2,3-O-isopropylidene-D-ribofuranose

Downstream raw materials:

N-(4S,5R)-benzyl-((2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)methylene)amine

(3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol

(1R,2S,6S,7S)-4,4,9-trimethyl-3,5,8-trioxa-9-aza-tricyclo[5.2.1.0^2,6]decane

(3aR,4S,6R,6aS)-6-anililino-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol

Refernces

• 1、 Gallos, John K.,Stathakis, Christos I.,Salapassidou, Maria J.,Grammatoglou, Constantinos E.,Koumbis, Alexandros E.. "A short alternative preparation of the bengazoles polyol side-chain segment". . p. 744 - 748. Retrieved 2007.
• 2、 -. "MEAYAMYCIN ANALOGUES AND METHODS OF USE". Page/Page column 5. . Retrieved 2021/10/15.
• 3、 Fan,Chuah,Jaenicke, Stephan. "A novel and environmental friendly synthetic route for hydroxypyrrolidines using zeolites". . p. 103 - 114. Retrieved 2018/12/13.