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Methanol → (3'r,4's,5s,5's,6'r)-3-[(4-Ethylphenyl)methyl]-6'-hydroxymethyl-3',4',5',6'-tetrahydro-spiro[furo[3,4,f]benzoisoxazole-5(7h),2'-[2h]pyran]-3',4',5'-triol

HRID 221939
Notes
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Reaction equation

HRID 221939 reaction equation
C([O:8][C@@H:9]1[C@@H:14]([O:15]CC2C=CC=CC=2)[C@@H:13]([O:23]CC2C=CC=CC=2)[C@@H:12]([CH2:31][O:32]CC2C=CC=CC=2)[O:11][C@:10]21[C:59]1[C:42](=[CH:43][C:44]3[O:48][N:47]=[C:46]([CH2:49][C:50]4[CH:55]=[CH:54][C:53]([CH2:56][CH3:57])=[CH:52][CH:51]=4)[C:45]=3[CH:58]=1)[CH2:41][O:40]2)C1C=CC=CC=1.CC1C(C)=C(C)C(C)=C(C)C=1.B(Cl)(Cl)Cl.CO>ClCCl>[CH2:56]([C:53]1[CH:54]=[CH:55][C:50]([CH2:49][C:46]2[C:45]3[CH:58]=[C:59]4[C@:10]5([C@H:9]([OH:8])[C@@H:14]([OH:15])[C@H:13]([OH:23])[C@@H:12]([CH2:31][OH:32])[O:11]5)[O:40][CH2:41][C:42]4=[CH:43][C:44]=3[O:48][N:47]=2)=[CH:51][CH:52]=1)[CH3:57]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887MethanolHCID 12784PentamethylbenzeneHCID 25135Boron TrichlorideHCID 68503405(3'r,4's,5s,5's,6'r)-3',4',5'-Tris-benzyloxy-6'-benzyloxymethyl-3-[(4-ethylphenyl)methyl]-3',4',5',6'-tetrahydro-spiro[furo[3,4,f]benzoisoxazole-5(7h),2'-[2h]pyran]

Product 1

HCID 24829535
(3'r,4's,5s,5's,6'r)-3-[(4-Ethylphenyl)methyl]-6'-hydroxymethyl-3',4',5',6'-tetrahydro-spiro[furo[3,4,f]benzoisoxazole-5(7h),2'-[2h]pyran]-3',4',5'-triol
Yield 48.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

(3′R,4′S,5S,5′S,6′R)-3′,4′,5′-tris-benzyloxy-6′-benzyloxymethyl-3-[(4-ethylphenyl)methyl]-3′,4′,5′,6′-tetrahydro-spiro[furo[3,4,f]benzoisoxazole-5(7H),2′-[2H]pyran] (86.9 mg, 0.110 mmol) was dissolved in dichloromethane (3.7 mL). Pentamethylbenzene (0.245 g, 1.65 mmol) was added thereto, and then this solution was cooled to −78° C. A solution of boron trichloride in dichloromethane (1.0 M, 0.55 mL) was added dropwise thereto. The resulting mixture was stirred for 2 hours, and then methanol (2.5 mL) was added thereto. The temperature of the mixture was raised to room temperature. The reaction mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel flash column chromatography (developing solution=methanol:dichloromethane (1:12)), to thereby obtain the titled compound (23.0 mg, 48%).

Workup

  1. temperatureThe temperature of the mixture was raised to room temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customThe resulting residue was purified by silica gel flash column chromatography (developing solution=methanol:dichloromethane (1:12))

Sources & evidence

ORD record
ord-23a20a21e36649748f2e82539f1792ba
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08207134B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes