Triethyl phosphite → HCID 22857244, compound

HRID 129110Notes

Reaction equation

[C:1]([O:4][C@H:5]1[CH2:18][C@H:17]([O:19][C:20](=[O:22])[CH3:21])[C@@H:16]([CH3:23])[O:15][C@:6]1([NH:24][C:25](=[O:28])[CH2:26]Cl)[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:3])[CH3:2].[P:29]([O:36]CC)([O:33][CH2:34][CH3:35])[O:30][CH2:31][CH3:32]>>[C:1]([O:4][C@H:5]1[CH2:18][C@H:17]([O:19][C:20](=[O:22])[CH3:21])[C@@H:16]([CH3:23])[O:15][C@:6]1([NH:24][C:25](=[O:28])[CH2:26][P:29]([O:33][CH2:34][CH3:35])([O:30][CH2:31][CH3:32])=[O:36])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:3])[CH3:2]

Participants

Reactant 2

HCID 31215Triethyl phosphite

HCID 54000904HCID 54000904, compound

Product 1

HCID 22857244HCID 22857244, compound

Procedure

Benzyl 2,4-di-O-acetyl-3,6-dideoxychloroacetamido-alpha-D-mannopyranoside, 20, 0.65 g (0.00157 mole) and triethyl phosphite (5 mL) were heated at 110°-120° C. for 4.5 h with stirring under argon. The solvent was distilled at high vacuum, 50 mg of the residue was saved, and the rest carried on.

Workup

distillationThe solvent was distilled at high vacuum, 50 mg of the residue

Sources & evidence

ORD record: ord-448fce20f3d84643a5c72ba2736690cf
Source dataset: uspto-grants-1995_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05466809

Reaction notes

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