HCID 12836809, compound → HCID 86736778, compound

HRID 2052237Notes

Reaction equation

HRID 2052237 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]([NH:5][C@@H:6]1[C@@H:13]([OH:14])[C@H:12]([CH3:15])[O:11][C@@H:8]([O:9]C)[CH2:7]1)=[O:4].[N+](=[CH2:20])=[N-].B(F)(F)F>C(Cl)Cl.C(Cl)(Cl)Cl>[CH3:20][O:14][C@H:13]1[C@H:12]([CH3:15])[O:11][CH:8]([OH:9])[CH2:7][C@@H:6]1[NH:5][C:3](=[O:4])[C:2]([F:17])([F:16])[F:1]

Participants

5

Reactant 2

HCID 12836809HCID 12836809, compoundHCID 87527742HCID 87527742, compound

Product 1

HCID 86736778HCID 86736778, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Treatment of 2.57 g; 10 mmoles of methyl 2,3,6-trideoxy-3-trifluoroacetamido-α-L-arabino-hexopyranoside (III-A) in methylene dichloride with diazomethane/boron-trifluoride, as described in Example I gave the corresponding 4-O-methylderivative (III-B, 1.7 g., 63%): m.p. 185°; [α]D23° =-101° (c=1, in CHCl3); mass spectrum m/e 271 (H+); pmr spectrum (CDCl3); 1.31 (d, CH3 --C--5), 3.30 and 3.43 (two s, OCH3) and 4.70δ (broad s, C--1--H). Acid hydrolysis of compound III-B as in Example I (1.63 g., 6 mmoles) gave 2,3,6-trideoxy-4-O-methyl-3-trifluoroacetamido-L-arabino-hexopyranose (III-C, 1.51 g., 98%): m.p. 201°; [α]D23° =-12.7° (c=0.48, in CHCl3); mass spectrum m/e 257 (M+).

Workup

  1. customgave the corresponding 4-O-methylderivative (III-B, 1.7 g., 63%)
  2. customAcid hydrolysis of compound III-B as in Example I (1.63 g., 6 mmoles)

Sources & evidence

ORD record
ord-aff1ef3739a84f12b712eb4dbf238c31
Source dataset
uspto-grants-1980_01
Patent number
US04183919

Reaction notes

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