Sodium Azide → HCID 53970366, compound

HRID 355479Notes

Reaction equation

HRID 355479 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[C@@H:25]([OH:26])[C@H:24]([OH:27])[C@@H:23]([CH2:28]OS(C2C=CC(C)=CC=2)(=O)=O)[O:22][C@@H:13]1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:40]=[N+:41]=[N-:42].[Na+]>CS(C)=O>[N:40]([CH2:28][C@H:23]1[O:22][C@H:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C@H:12]([NH:11][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[C@@H:25]([OH:26])[C@@H:24]1[OH:27])=[N+:41]=[N-:42]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 54544321HCID 54544321, compound

Product 1

HCID 53970366HCID 53970366, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 32.14 g benzyl 2-benzyloxycarbonylamino-2-desoxy-6-O-(p-tolylsulfonyl)-a-D-glucopyranoside in 75 ml of dimethyl sulfoxide was treated at room temperature with 7.5 g of sodium azide and stirred at 90° C. for 3 hours. The mixture was then poured on to ice/water. Separated crystals were filtered off under suction, washed with water and dried. There was obtained benzyl 6-azido-2-benzyloxycarbonylamino-2,6-didesoxy-a-D-glucopyranoside, [a]+119.60° (c 0.5; dioxan), MS: m/z 428 ([M+H]+).

Workup

  1. customSeparated crystals
  2. filtrationwere filtered off under suction
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-c544220d352645c1ac4e17f28562941e
Source dataset
uspto-grants-1998_11
Patent number
US05830920

Reaction notes

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