D-Glyceraldehyde synthesis
- Product Name:D-Glyceraldehyde
- CAS Number:453-17-8
- Molecular formula:C3H6O3
- Molecular Weight:90.08
1707-77-3
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453-17-8
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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]
96-26-4
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453-17-8
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591-57-1
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453-17-8
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57-04-5
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453-17-8
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453-17-8
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$25.00/100mg