2-Trans,6-trans,10-trans-geranylgeranyl diphosphate(3-) → syn-Copalyl diphosphate

HRID 2113253Notes

Reaction equation

[O:1]([CH2:10]/[CH:11]=[C:12](/[CH2:14][CH2:15]/[CH:16]=[C:17](\[CH3:29])/[CH2:18][CH2:19]/[CH:20]=[C:21](/[CH2:23][CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27])\[CH3:22])\[CH3:13])[P:2]([O:5][P:6]([O-:9])([O-:8])=[O:7])(=[O:4])[O-:3].C/C(/CC[C@H]1[C@@]2(C)CCCC(C)(C)[C@H]2CCC1=C)=C\CO>>[CH3:13]/[C:12](/[CH2:14][CH2:15][C@H:16]1[C@@:21]2([CH3:22])[CH2:23][CH2:24][CH2:25][C:26]([CH3:28])([CH3:27])[C@@H:20]2[CH2:19][CH2:18][C:17]1=[CH2:29])=[CH:11]\[CH2:10][O:1][P:2]([O:5][P:6]([OH:9])([OH:8])=[O:7])([OH:3])=[O:4]

Participants

Reactant 2

HCID 54971052-Trans,6-trans,10-trans-geranylgeranyl diphosphate(3-)

HCID 91697686Copalol

Product 1

HCID 5281991syn-Copalyl diphosphate

Procedure

Chemicals. The preparation of (E,E,E)-geranylgeranyl diphosphate (GGPP), and ent- and syn-copalyl diphosphate (CPP), from the corresponding copalol stereoisomers (Yee and Coates 1992), has been previously described (Mohan et al. 1996). Unless otherwise noted, all other chemicals were purchased from Fisher Scientific (Fairlawn, N.J., USA).

Sources & evidence

ORD record: ord-fc9042de1aa84f42b61ce73e68ff26cf
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07525016B1

Reaction notes

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