L-Ribose synthesis

10synthesis methods

Product Name:L-Ribose
CAS Number:24259-59-4
Molecular formula:C5H10O5
Molecular Weight:150.13

A method for converting inexpensive, naturally occurring D-ribose into L-ribose is by interconverting the hydroxy group at Cl and the hydroxymethyl group at C5. L-Ribose is prepared from D-ribose by (a) forming a hydroxy-protected D-ribose, (b) reducing the hydroxy-protected D-ribose to a protected tetrol, (c) converting the tetrol to a tetraester, such as a tetraacetate; (d) hydrolyzing the protecting group to form a hydroxymethyl tetraester; (e) oxidizing the hydroxymethyl group to form a tetraester aldehyde; and (f) hydrolysing the ester groups to yield L-ribose.

Olean-12-en-28-oic acid, 3-(β-D-glucopyranosyloxy)-23-(α-D-ribofuranosyloxy)-, (3β,4α)-

1500092-25-0
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50-69-1 Synthesis

50-69-1
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$5.00/5g

24259-59-4
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$5.00/1g

50-99-7 Synthesis

50-99-7
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$6.00/25g

921-60-8 Synthesis

921-60-8
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Yield:-

Reaction Conditions:

with trifluoroacetic acid in water at 120; for 4 h;

Steps:

Acid hydrolysis of compound 1

Compound 1 (about 4 mg) was added into a solution of water (1 mL) and 2N aqueous CF₃COOH(2 mL), heated to 120°C under reflux conditions for 4 h. The mixture was diluted with water (2 mL) and then extracted with EtOAc (3 ￡2 mL). The combined organic phase was washed with brine and evaporated to dryness to afford the aglycones. The aqueous phase was concentrated. Then dry pyridine (1 mL) and L-cysteine methyl ester hydrochloride (2 mg) were added into the residue. Each mixture was reacted at 60°C for 1 h, and 0.5mL of (trimethylsilyl) imidazole dissolved in H2O was added, followed by heating to dryness at 60°C for 2 h. Each dried reactant was extracted with n-hexane (3 ￡ 1 mL) and H₂O (1 mL, each). The n-hexane fraction was subjected to GC (column: Rtx-1, 0.25mm i.d. 0.25 mm, length 30 m). The conditions of GC were flame ionization detector; column temperature 100-180°C (10°C min-1)and 180-230°C (3°C min21); injector temperature 250°C; detector temperature 300°C and the carrier gas (N₂, 0.8mLmin21). Under these conditions, these sugars of each reactants were identified by comparison with authentic samples: t_R (min) 7.56 (D-ribose), 7.85 (L-ribose), 10.49 (D-glucose) and 11.10 (L-glucose).

References:

Shu, Zhan;Chen, Zhong;Liu, Yan-Li;Zhu, Wei-Feng;Feng, Yu-Lin;Xu, Qiong-Ming;Li, Xiao-Ran;Yang, Shi-Lin [Natural Product Research,2013,vol. 27,# 23,p. 2196 - 2201]