Azobisisobutyronitrile → 3,6-anhydro-1,2-dideoxy-1-(diethoxyphosphinyl)-1,1-difluoro-4,5,7-tris-O-(phenylmethyl)-D-manno-heptitol

HRID 2166291Notes

Reaction equation

HRID 2166291 reaction equation
[CH2:1]([O:3][P:4]([O:41][CH2:42][CH3:43])([C:6]([F:40])([F:39])[C@@H:7]([C@H:9]1[O:29][C@H:28]([CH2:30][O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C@@H:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C@@H:10]1[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)O)=[O:5])[CH3:2].C(OP(OCC)(C(F)(F)[C@@H](O)[C@H]1O[C@H](COCC2C=CC=CC=2)[C@@H](OCC2C=CC=CC=2)[C@@H]1OCC1C=CC=CC=1)=O)C.N(C(C)(C)C#N)=NC(C)(C)C#N>C1(C)C=CC=CC=1>[CH2:42]([O:41][P:4]([O:3][CH2:1][CH3:2])([C:6]([F:40])([F:39])[CH2:7][C@H:9]1[O:29][C@H:28]([CH2:30][O:31][CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C@@H:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C@@H:10]1[O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:5])[CH3:43]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 886089602,5-anhydro-7-deoxy-7-(diethoxyphosphinyl)-7,7-difluoro-1,3,4-tris-O-(phenylmethyl)-D-glycero-D-manno-heptitolHCID 886090023,6-anhydro-1-deoxy-1-(diethoxyphosphinyl)-1,1-difluoro-4,5,7-tris-O-(phenylmethyl)-D-glycero-D-galacto-heptitol

Product 1

HCID 151171743,6-anhydro-1,2-dideoxy-1-(diethoxyphosphinyl)-1,1-difluoro-4,5,7-tris-O-(phenylmethyl)-D-manno-heptitol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 440 mg portion of a mixture of 3,6-anhydro-1-deoxy-1-(diethoxyphosphinyl)-1,1-difluoro-4,5,7-tris-O-(phenylmethyl)-D-glycero-D-galacto-heptitol, O-1H-imidazole-1-carbothioate and 2,5-anhydro-7-deoxy-7-(diethoxyphosphinyl)-7,7-difluoro-1,3,4-tris-O-(phenylmethyl)-D-glycero-D-manno-heptitol, O-1H-imidazole-1-carbothioate was dissolved in 12 ml of dry toluene, then treated with 900 μl of n-tributyl stannous hydride and a few crystals of 2,2'-azobisisobutyronitrile and heated in an oil bath under argon for 3 hours. The solution was cooled, then stored in a freezer and finally evaporated. The resulting oil was purified by chromatography giving the desired compound.

Workup

  1. temperatureThe solution was cooled
  2. customfinally evaporated
  3. customThe resulting oil was purified by chromatography

Sources & evidence

ORD record
ord-951357c0d796462e9fdcf8ded0b1b03b
Source dataset
uspto-grants-1990_07
Patent number
US04943629

Reaction notes

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