Dichloromethane → HCID 59235383, compound

HRID 2174337Notes

Reaction equation

S(Cl)(Cl)=O.[Cl:5][C:6]1[C:7]([CH2:53][C:54]2[CH:59]=[CH:58][C:57]([O:60][CH2:61][CH3:62])=[CH:56][CH:55]=2)=[CH:8][C:9]([C@H:14]2[C@H:19]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C@@H:18]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C@H:17]([O:36][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[C@@H:16]([CH2:44][O:45][CH2:46][C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[O:15]2)=[C:10](CO)[CH:11]=1.[CH2:63]([Cl:65])Cl>>[CH2:37]([O:36][C@H:17]1[C@H:18]([O:28][CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C@@H:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C@H:14]([C:9]2[CH:8]=[C:7]([CH2:53][C:54]3[CH:55]=[CH:56][C:57]([O:60][CH2:61][CH3:62])=[CH:58][CH:59]=3)[C:6]([Cl:5])=[CH:11][C:10]=2[CH2:63][Cl:65])[O:15][C@@H:16]1[CH2:44][O:45][CH2:46][C:47]1[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

Reactant 3

HCID 6344Dichloromethane

HCID 24386Thionyl Chloride

HCID 67072925HCID 67072925, compound

Product 1

HCID 59235383HCID 59235383, compound

Procedure

Thionyl chloride (0.1 mL) was added dropwise into a solution of (5-chloro-4-(4-ethoxybenzyl)-2-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)methanol (100 mg, 0.13 mmol) in methylene chloride (2 mL) at 0° C., and the mixture was allowed to stir for 2 hours at RT. The reaction mixture was evaporated to dryness, and the residual oil was used for the next step without further purification.

Workup

customThe reaction mixture was evaporated to dryness
customthe residual oil was used for the next step without further purification

Sources & evidence

ORD record: ord-d3dcc29df88b4298a122af58a7d991e9
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09061060B2

Reaction notes

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