ChemicalBook CAS DataBase List D-Glyceraldehyde

D-Glyceraldehyde synthesis

7synthesis methods

Product Name:D-Glyceraldehyde
CAS Number:453-17-8
Molecular formula:C3H6O3
Molecular Weight:90.08

1707-77-3 Synthesis

1,2:5,6-Bis-O-(1-methylethylidene)-D-mannitol

1707-77-3
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$5.00/5g

453-17-8
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$25.00/100mg

Yield:453-17-8 18 g

Reaction Conditions:

with sodium periodate;sodium hydrogencarbonate in dichloromethane at 0 - 20; for 5 h;

Steps:

1S)-1-[(2R)-1,4-Dioxaspiro[4.5]dec-2-yl]-3-buten-1-ol (5).
To a cooled (0 oC) solution of mannitol diacetonide(20 g, 58.47 mmol) in CH2Cl2 (100 mL), NaIO4 (25.02 g, 116.95 mmol) followed by sat. NaHCO3 (8 mL) wereadded and stirred at room temperature for 5 h. Reaction mixture was dried (Na2SO4), filtered and evaporatedunder reduced pressure to give (R)-Glyceraldehyde (18 g) and used as such to next reaction.To a stirred and cooled (0 oC) mixture of (R)-Glyceraldehyde (18 g, 105.26 mmol) and dry Zinc (13.7 g, 210.50mmol) in THF (100 mL), allyl bromide (10.7 mL, 126.30 mmol) was added very slowly for 15 min, followed bythe addition of sat. NH4Cl (72 mL) solution. After 6 h, reaction mixture was diluted with excess sat. NH4Clsolution (50 mL) and extracted with ethyl acetate (2 x 100 mL). The organic layers were washed with water (2x 20 mL), brine (20 mL), dried (Na2SO4), evaporated under reduced pressure and purified the residue bycolumn chromatography (Silica gel, 60-120 mesh, 5% EtOAc in pet. ether) to furnish 5 (17.5 g, 78%) as a yellowliquid. [a]D +1.7 (c 2.5, CHCl3); IR (neat): 2985, 2936, 2863, 1613, 1513 cm-1; 1H NMR (CDCl3, 500 MHz) δ (ppm):5.87-5.77 (m, 2H), 5.14-5.10 (m, 2H), 3.98-3.91 (m, 2H), 3.89-3.85 (m, 1H), 3.72-3.69 (m, 1H), 2.23-2.14 (m,2H), 1.60-1.55 (m, 8H), 1.41-1.38 (m, 2H); ESIMS: 235 (M+ Na)+, 213 (M + H).

References:

Bommagani, Shobanbabu;Thodupunuri, Prashanth;Sharma, Gangavaram V.M. [Arkivoc,2017,vol. 2017,# 4,p. 20 - 33]

FullText

96-26-4 Synthesis