Mannitol → Mannitol monocarbonate

HRID 2252416Notes

Reaction equation

CC1C(=[O:8])[C@@H](O)CC(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1C(C)(C)C[C@H](O)C(=O)C=1C.CCN(C(C)C)C(C)C.Cl[C:55]([O:57]C(Cl)C(Cl)(Cl)Cl)=[O:56].[CH2:64]([OH:75])[C@H:65]([C@H:67]([C@@H:69]([C@@H:71]([CH2:73][OH:74])[OH:72])[OH:70])[OH:68])[OH:66]>C(Cl)Cl.CN(C1C=CN=CC=1)C.CN(C=O)C>[C:55](=[O:56])([OH:8])[OH:57].[CH2:73]([OH:74])[C@H:71]([C@H:69]([C@@H:67]([C@@H:65]([CH2:64][OH:75])[OH:66])[OH:68])[OH:70])[OH:72]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of astaxanthin 2E (0.100 g, 0.168 mmol) in DCM (4 mL) at 0° C. was added DIPEA (0.585 mL, 3.36 mmol), and 1,2,2,2-tetrachloroethyl chloroformate (0.103 mL, 0.672 mmol). The reaction mixture was stirred at 0° C. for 2 hours, then at room temperature for 1.5 hours, at which time (D)-mannitol (0.3060 g, 1.68 mmol), DMF (3 mL), and DMAP (0.2052 g, 1.68 mmol) were added to the reaction. The reaction mixture was stirred at room temperature for 24 hours, at which time the reaction was diluted with DCM, quenched with brine (20 mL), and then extracted with DCM. The combined organic layers were concentrated to yield mannitol monocarbonate (LVII) (10.19%) HPLC retention time: 9.474 min., 10.19% (AUC); LRMS (ESI) m/z (relative intensity): 827 (M++Na) (50), 804 (M+) (25), 725 (58), 613 (100), and as (53.73%).

Workup

waitat room temperature for 1.5 hours
stirringThe reaction mixture was stirred at room temperature for 24 hours, at which time the reaction
customquenched with brine (20 mL)
extractionextracted with DCM
concentrationThe combined organic layers were concentrated

Sources & evidence

ORD record: ord-3cda3aee046742a5920a2394d3eda78f
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07320997B2

Reaction notes

Loading…