HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Tributylphosphine → 1-(4-Cyclopropylphenyl)methyl-2-[(1R,4R,5S,6S)-4,5,6-trisbenzyloxy-3-(benzyloxymethyl)-cyclohex-2-enyloxy]benzene

HRID 554563
Notes
Print preview

Reaction equation

HRID 554563 reaction equation
[CH:1]1([C:4]2[CH:17]=[CH:16][C:7]([CH2:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[OH:15])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.C(P(CCCC)CCCC)CCC.[CH2:31]([O:38][C@H:39]1[C@H:44]([O:45][CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C@@H:43]([O:53][CH2:54][C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[C@@H:42](O)[CH:41]=[C:40]1[CH2:62][O:63][CH2:64][C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.CN(C(/N=N/C(N(C)C)=O)=O)C>C1(C)C=CC=CC=1.CCCCCC>[CH:1]1([C:4]2[CH:17]=[CH:16][C:7]([CH2:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15][C@H:42]3[C@H:43]([O:53][CH2:54][C:55]4[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=4)[C@@H:44]([O:45][CH2:46][C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)[C@H:39]([O:38][CH2:31][C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[C:40]([CH2:62][O:63][CH2:64][C:65]4[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=4)=[CH:41]3)=[CH:6][CH:5]=2)[CH2:2][CH2:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 13831TributylphosphineHCID 5353800DiamideHCID 11432631(1S,4R,5S,6S)-4,5,6-tris(benzyloxy)-3-(benzyloxymethyl)cyclohex-2-enolHCID 674614742-(4-Cyclopropylbenzyl)phenol

Product 1

HCID 674611171-(4-Cyclopropylphenyl)methyl-2-[(1R,4R,5S,6S)-4,5,6-trisbenzyloxy-3-(benzyloxymethyl)-cyclohex-2-enyloxy]benzene
Yield 62%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

In a nitrogen stream, 2-(4-cyclopropylbenzyl)phenol and tributylphosphine (70 μL, 0.28 mmol) were added to a solution of (1S,4R,5S,6S)-4,5,6-tris(benzyloxy)-3-(benzyloxymethyl)cyclohex-2-enol (51 mg, 0.095 mmol) as described in a document [J. Org. Chem., 63, 5668-5671 (1998)] in toluene (300 μL) under cooling with ice, and then tetramethylazodicarboxamide (48 mg, 0.28 mmol) was added thereto at the same temperature. The reaction mixture was stirred at the same temperature for 20 hours and then hexane was added thereto and the precipitate was filtered and the solvent of the filtrate was distilled. The obtained residue was purified by preparative TLC [developing solution=ethyl acetate:n-hexane (1:5) to obtain the title compound (44 mg, 62%).

Workup

  1. temperatureunder cooling with ice
  2. filtrationthe precipitate was filtered
  3. distillationthe solvent of the filtrate was distilled
  4. customThe obtained residue was purified by preparative TLC [

Sources & evidence

ORD record
ord-a367b2c831964a86a98f07df5923cfa5
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08048897B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes