Bromomethyl acetate → HCID 78324451, compound

HRID 522169Notes

Reaction equation

[C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:8]([CH3:19])[O:7][C@@H:6]1[CH2:20][P:21]([O:32][CH2:33][O:34][C:35](=[O:40])[C:36](C)(C)C)([O:23][CH2:24][O:25][C:26](=[O:31])[C:27](C)(C)C)=[O:22])(=[O:3])[CH3:2].C(OCBr)(=O)C.C(OCI)(=O)C(C)(C)C>>[C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:8]([CH3:19])[O:7][C@@H:6]1[CH2:20][P:21]([O:32][CH2:33][O:34][C:35](=[O:40])[CH3:36])([O:23][CH2:24][O:25][C:26](=[O:31])[CH3:27])=[O:22])(=[O:3])[CH3:2]

Participants

Reactant 3

HCID 68536Bromomethyl acetate

HCID 104401Iodomethyl pivalate

HCID 78324148HCID 78324148, compound

Product 1

HCID 78324451HCID 78324451, compound

Procedure

This compound was synthesized by the same procedure used for the synthesis of (2S,3S,4R,5R,6S)-2-((bis((pivaloyloxy)methoxy)phosphoryl)methyl)-6-methyltetrahydro-2H-pyran-3,4,5-triyl triacetate, but using bromomethyl acetate (commercially available from Sigma Aldrich) instead of iodomethyl pivalate: ESI (M+H) 513.0; calc for C19H29O14P 512.4; 1H NMR (400 MHz, CD3OD) δ ppm 5.71-5.61 (m, 4 H) 5.29 (dd, J=3.33, 0.78 Hz, 1 H) 5.12 (dd, J=3.33, 10.17 Hz, 1 H) 5.05 (dd, J=9.59, 9.98 Hz, 1 H) 4.00-3.83 (m, 2 H) 2.35-2.17 (m, 2 H) 2.18 (s, 3 H) 2.16 (s, 3 H) 2.15 (s, 3 H) 2.09 (s, 3 H) 1.96 (2, 3 H) 1.18 (d, J=6.46 Hz, 3 H).

Workup

customThis compound was synthesized by the same procedure

Sources & evidence

ORD record: ord-652c00e6ac484751903f9d66a01fbe37
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328134B2

Reaction notes

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