Triphenylphosphine → HCID 88065726, compound

HRID 1369900Notes

Reaction equation

HRID 1369900 reaction equation
[C:1]1([CH:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[O:8][C:9]2[C:14]3[CH:15]=[CH:16][C:17]([OH:20])=[C:18]([CH3:19])[C:13]=3[O:12][C:11](=[O:21])[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:28][C:29]1([CH3:40])[O:35][CH:33](O)[C@H:32]([OH:36])[C@H:31]([OH:37])[C@H:30]1[O:38][CH3:39].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>ClCCl>[CH3:28][C:29]1([CH3:40])[O:35][C@@H:33]([O:20][C:17]2[CH:16]=[CH:15][C:14]3[C:9]([O:8][CH:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:10][C:11](=[O:21])[O:12][C:13]=3[C:18]=2[CH3:19])[C@H:32]([OH:36])[C@H:31]([OH:37])[C@H:30]1[O:38][CH3:39]

Participants

6

Reactant 4

HCID 11776Triphenylphosphine3×HCID 5363146Diisopropyl azodicarboxylate3×HCID 10442556HCID 10442556, compoundHCID 11348891HCID 11348891, compound

Product 1

HCID 88065726HCID 88065726, compoundYield 63.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 91.13 g of the product of Stage B, 58.6 g of 6-deoxy-5-C-methyl-4-O-methyl-L-lyxo-hexopyranose and 80 g of triphenylphosphine in 900 ml of dichloromethane is cooled down to 0° C. 60 ml of diisopropylazodicarboxylate is added dropwise. Agitation is carried out for 1 hour at ambient temperature. 34 g of triphenylphosphine and 25 ml of diisopropylazodicarboxylate are added. Agitation is carried out for 1 hour at ambient temperature. 34 g of triphenylphosphine and 25 ml of diisopropylazodicarboxylate are added and agitation is carried out for 12 hours at ambient temperature. The reaction medium is concentrated under vacuum then chromatographed eluting with a toluene/isopropyl alcohol mixture (95-5). After combining the fractions, evaporating the solvents, and recrystallization from isopropyl ether, 86.33 g of sought product is obtained.

Workup

  1. waitAgitation is carried out for 1 hour at ambient temperature
  2. waitagitation is carried out for 12 hours at ambient temperature
  3. concentrationThe reaction medium is concentrated under vacuum
  4. customthen chromatographed
  5. washeluting with a toluene/isopropyl alcohol mixture (95-5)
  6. customevaporating
  7. customthe solvents, and recrystallization from isopropyl ether

Sources & evidence

ORD record
ord-f63cbadbb46947e6976dab9964ed6eec
Source dataset
uspto-grants-2003_06
Patent number
US06579902B1

Reaction notes

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