CAS No.110567-22-1,(1S,2R,3S,5R)-3-(Phenymethyloxy)-2-(phenylmethoxy)methyl-6-oxabicyclo[3.1.0]hexane Suppliers

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Basic Information

Molecular Structure:
CAS No.:	110567-22-1
Name:	(1S,2R,3S,5R)-3-(Phenymethyloxy)-2-(phenylmethoxy)methyl-6-oxabicyclo[3.1.0]hexane
Article Data:	8

Formula:	C₂₀H₂₂O₃
Molecular Weight:	310.393
Synonyms:	(1S,2R,3S,5R)-3-(Benzyloxy)-2-[(benzyloxy)methyl]-6-oxabicyclo[3.1.0]hexane;
EINECS:	1592732-453-0
Density:	1.174 g/cm³
Boiling Point:	427.928 °C at 760 mmHg
Flash Point:	145.852 °C
Safety:	24/25
PSA:	30.99000
LogP:	3.57590

Synthetic route

: 100-39-0
benzyl bromide

: 117641-39-1
(2R,3S)-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexan-3-ol

: 110567-22-1
(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

Conditions

Conditions	Yield
Stage #1: (2R,3S)-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexan-3-ol With sodium hydride In tetrahydrofuran at 20℃; for 1h; Stage #2: benzyl bromide With tetra-(n-butyl)ammonium iodide In tetrahydrofuran at 20℃; for 12h;	86%
With tetra-(n-butyl)ammonium iodide; sodium hydride 1.) THF, 2 h; 1.) THF, 2.5 h; Yield given. Multistep reaction;
With tetra-(n-butyl)ammonium iodide; sodium hydride In N,N-dimethyl-formamide Yield given;
With tetra-(n-butyl)ammonium iodide; sodium hydride In N,N-dimethyl-formamide; mineral oil at -50℃; for 18h;
With sodium hydride In tetrahydrofuran; water at 20℃; Large scale;	4.4 kg

: 3587-60-8
Benzyloxymethyl chloride

: 110567-22-1
(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: NaH / tetrahydrofuran / 1 h / 0 °C 1.2: tetrahydrofuran / 2 h / -40 °C 2.1: (-)-diisopinocamphenylborane / tetrahydrofuran / 17 h / -60 - 0 °C 2.2: 8.20 g / aq. NaOH; H2O2 / diethyl ether; tetrahydrofuran / 12 h / 0 °C 3.1: 82 percent / Mo(CO)6; t-BuOOH / benzene; decane / 3 h / 80 °C 4.1: NaH / tetrahydrofuran / 1 h / 20 °C 4.2: 86 percent / tetrabutylammonium iodide / tetrahydrofuran / 12 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1: tetrahydrofuran / -78 - -65 °C 2: 1.) diisopinylcampheylborane (prepared from (+)-α-pinene), 2.) aq. NaOH, H2O2 / 1.) THF, -65 to -78 deg C 3: VO(acac)2, t-BuOOH / CH2Cl2 4: NaH, Bu4NI / dimethylformamide View Scheme
Multi-step reaction with 4 steps 1: 1.) Na / 1.) THF, -5 deg C, 1.5 h; 2.) THF, -45 deg C, 1 h 2: 15.8 g / (-)-diisopinan-3-ylborane / tetrahydrofuran / 1.) -60 deg C, 1 h; 2.) 5 deg C, 18 h 3: 12.0 g / t-butyl hydroperoxide, vanadium(V)acetylacetonate / 1,2-dichloro-ethane / 2.75 h / 30 °C 4: 1.) NaH; 2.) tetrabutylammonium iodide / 1.) THF, 2 h; 1.) THF, 2.5 h View Scheme

: 39939-07-6
5-(benzyloxymethyl)cyclopentadiene

: 110567-22-1
(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: (-)-diisopinocamphenylborane / tetrahydrofuran / 17 h / -60 - 0 °C 1.2: 8.20 g / aq. NaOH; H2O2 / diethyl ether; tetrahydrofuran / 12 h / 0 °C 2.1: 82 percent / Mo(CO)6; t-BuOOH / benzene; decane / 3 h / 80 °C 3.1: NaH / tetrahydrofuran / 1 h / 20 °C 3.2: 86 percent / tetrabutylammonium iodide / tetrahydrofuran / 12 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: 1.) diisopinylcampheylborane (prepared from (+)-α-pinene), 2.) aq. NaOH, H2O2 / 1.) THF, -65 to -78 deg C 2: VO(acac)2, t-BuOOH / CH2Cl2 3: NaH, Bu4NI / dimethylformamide View Scheme
Multi-step reaction with 3 steps 1: 15.8 g / (-)-diisopinan-3-ylborane / tetrahydrofuran / 1.) -60 deg C, 1 h; 2.) 5 deg C, 18 h 2: 12.0 g / t-butyl hydroperoxide, vanadium(V)acetylacetonate / 1,2-dichloro-ethane / 2.75 h / 30 °C 3: 1.) NaH; 2.) tetrabutylammonium iodide / 1.) THF, 2 h; 1.) THF, 2.5 h View Scheme

: 542-92-7
cyclopenta-1,3-diene

(AsCF3)4.5: (AsCF3)4.5

: 110567-22-1
(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

Conditions

Yield

Multi-step reaction with 4 steps
1.1: NaH / tetrahydrofuran / 1 h / 0 °C
1.2: tetrahydrofuran / 2 h / -40 °C
2.1: (-)-diisopinocamphenylborane / tetrahydrofuran / 17 h / -60 - 0 °C
2.2: 8.20 g / aq. NaOH; H2O2 / diethyl ether; tetrahydrofuran / 12 h / 0 °C
3.1: 82 percent / Mo(CO)6; t-BuOOH / benzene; decane / 3 h / 80 °C
4.1: NaH / tetrahydrofuran / 1 h / 20 °C
4.2: 86 percent / tetrabutylammonium iodide / tetrahydrofuran / 12 h / 20 °C
View Scheme

: 110567-21-0
(1S,2R)-2-(benzyloxymethyl)-1-hydroxy-3-cyclopentene

: 110567-22-1
(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 82 percent / Mo(CO)6; t-BuOOH / benzene; decane / 3 h / 80 °C 2.1: NaH / tetrahydrofuran / 1 h / 20 °C 2.2: 86 percent / tetrabutylammonium iodide / tetrahydrofuran / 12 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: VO(acac)2, t-BuOOH / CH2Cl2 2: NaH, Bu4NI / dimethylformamide View Scheme
Multi-step reaction with 2 steps 1: 12.0 g / t-butyl hydroperoxide, vanadium(V)acetylacetonate / 1,2-dichloro-ethane / 2.75 h / 30 °C 2: 1.) NaH; 2.) tetrabutylammonium iodide / 1.) THF, 2 h; 1.) THF, 2.5 h View Scheme
Multi-step reaction with 2 steps 1.1: tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium / dichloromethane / 16 h / 20 °C / Large scale 1.2: 1 h / 20 °C / Large scale 2.1: sodium hydride / water; tetrahydrofuran / 20 °C / Large scale View Scheme

: 4984-82-1
sodium cyclopentadienylide

: 110567-22-1
(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: tetrahydrofuran / -78 - -65 °C 2: 1.) diisopinylcampheylborane (prepared from (+)-α-pinene), 2.) aq. NaOH, H2O2 / 1.) THF, -65 to -78 deg C 3: VO(acac)2, t-BuOOH / CH2Cl2 4: NaH, Bu4NI / dimethylformamide View Scheme

: 542-92-7
cyclopenta-1,3-diene

: 110567-22-1
(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.) Na / 1.) THF, -5 deg C, 1.5 h; 2.) THF, -45 deg C, 1 h 2: 15.8 g / (-)-diisopinan-3-ylborane / tetrahydrofuran / 1.) -60 deg C, 1 h; 2.) 5 deg C, 18 h 3: 12.0 g / t-butyl hydroperoxide, vanadium(V)acetylacetonate / 1,2-dichloro-ethane / 2.75 h / 30 °C 4: 1.) NaH; 2.) tetrabutylammonium iodide / 1.) THF, 2 h; 1.) THF, 2.5 h View Scheme

: 110567-22-1
(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

: 117641-42-6
(1S,2R,3S,5R)-2-Hydroxymethyl-6-oxa-bicyclo[3.1.0]hexan-3-ol

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal	100%

: 110567-22-1
(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

: 110567-23-2
(1S,2S,3S,5S)-5-azido-3-(benzyloxy)-2-(benzyloxymethyl)cyclopentanol

Conditions

Conditions	Yield
With sodium azide; ammonium chloride In ethanol at 85℃; for 22h;	99%
With sodium azide; ammonium chloride In ethanol at 85℃; for 22h;

: 1351691-90-1
C17H19N5O3

: 110567-22-1
(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

: C37H41N5O6

Conditions

Conditions	Yield
Stage #1: C17H19N5O3 With lithium hydride In N,N-dimethyl-formamide at 60℃; for 0.25h; Stage #2: (2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane In N,N-dimethyl-formamide at 125℃; for 2.5h;	83%

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Specification

The CAS registry number of (1S,2R,3S,5R)-3-(Phenymethyloxy)-2-(phenylmethoxy)methyl-6-oxabicyclo[3.1.0]hexane is 110567-22-1. The molecular formula is C₂₀H₂₂O₃ and the molecular weight is 310.39. In addition, the systematic name is (1S,2R,3S,5R)-3-(benzyloxy)-2-[(benzyloxy)methyl]-6-oxabicyclo[3.1.0]hexane. It belongs to the classes of Intermediates; Intermediates & Fine Chemicals; Pharmaceuticals. What's more, it should be stored in sealed container, and put in a cool and dry place.

Physical properties about this chemical are: (1)ACD/LogP: 3.58; (2)ACD/LogD (pH 5.5): 4; (3)ACD/LogD (pH 7.4): 4; (4)ACD/BCF (pH 5.5): 1200; (5)ACD/BCF (pH 7.4): 1200; (6)ACD/KOC (pH 5.5): 5569; (7)ACD/KOC (pH 7.4): 5569; (8)#H bond acceptors: 3; (9)#Freely Rotating Bonds: 7; (10)Polar Surface Area: 30.99 Å²; (11)Index of Refraction: 1.593; (12)Molar Refractivity: 89.559 cm³; (13)Molar Volume: 264.428 cm³; (14)Polarizability: 35.504 ×10^-24cm³; (15)Surface Tension: 46.879 dyne/cm; (16)Density: 1.174 g/cm³; (17)Flash Point: 145.852 °C; (18)Enthalpy of Vaporization: 65.656 kJ/mol; (19)Boiling Point: 427.928 °C at 760 mmHg.

You can still convert the following datas into molecular structure:
(1)SMILES: O(Cc1ccccc1)[C@@H]2[C@H]([C@@H]3O[C@@H]3C2)COCc4ccccc4
(2)InChI: InChI=1/C20H22O3/c1-3-7-15(8-4-1)12-21-14-17-18(11-19-20(17)23-19)22-13-16-9-5-2-6-10-16/h1-10,17-20H,11-14H2/t17-,18+,19-,20+/m1/s1
(3)InChIKey: YPDRJNPIGFCETD-WCIQWLHIBP