Phosphonic acid, [(triphenylphosphoranylidene)methyl]-, diphenyl ester → HCID 131716488, compound

HRID 2166490Notes

Reaction equation

HRID 2166490 reaction equation
[C:1]1([CH2:7][O:8][C@H:9]2[C@H:15]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C@@H:14]([CH2:24][O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[O:13][C@@H:10]2[CH:11]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(=[CH:52][P:53](=[O:68])([O:61][C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=2)[O:54][C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[O:61]([P:53]([O:54][C:55]1[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=1)([CH:52]=[CH:11][C@H:10]1[O:13][C@H:14]([CH2:24][O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C@@H:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@@H:9]1[O:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:68])[C:62]1[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=1

Participants

4

Reactant 2

HCID 631810Phosphonic acid, [(triphenylphosphoranylidene)methyl]-, diphenyl esterHCID 108364862,5-anhydro-3,4,6-tris-O-(phenylmethyl)-D-mannose

Product 1

HCID 131716488HCID 131716488, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

An 880 mg portion of 2,5-anhydro-3,4,6-tris-O-(phenylmethyl)-D-mannose was dissolved in 6 ml of dry toluene and treated with 1.11 g of diphenyl triphenylphosphoranylidenemethylphosphonate at reflux temperature for 36 hours. Purification by chromatography, eluting with hexane:ethyl acetate afforded 660 mg of the desired compound.

Workup

  1. temperatureat reflux temperature for 36 hours
  2. customPurification by chromatography
  3. washeluting with hexane

Sources & evidence

ORD record
ord-39b59703f37c4812baa3f8626d6ab396
Source dataset
uspto-grants-1990_07
Patent number
US04945158

Reaction notes

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