Dichloromethane → 1,2-Anhydro-3,5-di-O-(p-toluoyl)-2-C-methyl-alpha-D-ribofuranose

HRID 1391975Notes

Reaction equation

ClCCl.[CH3:4][C@@:5]1([OH:32])[C@H:10]([O:11][C:12]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)=[O:13])[C@@H:9]([CH2:21][O:22][C:23]([C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=2)=[O:24])[O:8][CH:6]1O.CS(Cl)(=O)=O>C(N(CC)CC)C>[C:28]1([CH3:31])[CH:29]=[CH:30][C:25]([C:23]([O:22][C@@H:21]2[C@@H:9]([CH2:10][O:11][C:12]([C:14]3[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=3)=[O:13])[O:8][C@@H:6]3[O:32][C@:5]23[CH3:4])=[O:24])=[CH:26][CH:27]=1

Participants

Conditions

Temperature: 30 °C

Procedure

To a 72 L vessel was charged dry dichloromethane (32 L), triethylamine (3.0 L), and diol 2-2 (3.44 kg, 90 wt % pure). The mixture was warmed to 30° C., then methanesulfonyl chloride (0.79 L) was added over 40 min. After 1 h, the batch was partitioned between pH 7 buffer (20 L) and methyl tert-butyl ether (44 L). The organic phase was washed with 1M aqueous NaCl (38 L) then switched to toluene by vacuum distillation followed by concentration to about 9 L. The resulting solution of epoxide was used directly in Step B.

Workup

customthe batch was partitioned between pH 7 buffer (20 L) and methyl tert-butyl ether (44 L)
washThe organic phase was washed with 1M aqueous NaCl (38 L)
distillationthen switched to toluene by vacuum distillation
concentrationfollowed by concentration to about 9 L

Sources & evidence

ORD record: ord-f8eb0a5ad75a42cebef75de879569ea1
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07339054B2

Reaction notes

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