(3aR,4R,5R,6R,6aS)-2-(dimethylamino)-6-(phenylmethoxymethyl)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]oxazole-4,5-diol

Base Information

• Chemical Name: (3aR,4R,5R,6R,6aS)-2-(dimethylamino)-6-(phenylmethoxymethyl)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]oxazole-4,5-diol
• CAS No.: 134875-86-8
• Molecular Formula: C₁₆H₂₂N₂O₄
• Molecular Weight: 306.362
• DSSTox Substance ID: DTXSID60928791
• Nikkaji Number: J702.809A
• Wikidata: Q82903609
• Mol file: 134875-86-8.mol

Synonyms:134875-86-8;DTXSID60928791;4H-Cyclopentoxazole-4,5-diol, 2-(dimethylamino)-3a,5,6,6a-tetrahydro-6-[(phenylmethoxy)methyl]-, (3aR,4R,5R,6R,6aS)-;(1S,5R,6R)-3-(Dimethylamino)-8beta-(benzyloxymethyl)-2-oxa-4-azabicyclo[3.3.0]oct-3-ene-6beta,7alpha-diol;6-[(Benzyloxy)methyl]-2-(dimethylamino)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]oxazole-4,5-diol

Chemical Property of (3aR,4R,5R,6R,6aS)-2-(dimethylamino)-6-(phenylmethoxymethyl)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]oxazole-4,5-diol

Chemical Property:

• Boiling Point: 432.9±55.0 °C(Predicted)
• PKA: 13.44±0.70(Predicted)
• Density: 1.35±0.1 g/cm3(Predicted)
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 306.15795719
• Heavy Atom Count: 22
• Complexity: 409

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CN(C)C1=NC2C(C(C(C2O1)COCC3=CC=CC=C3)O)O
• Isomeric SMILES: CN(C)C1=N[C@@H]2[C@H]([C@@H]([C@H]([C@@H]2O1)COCC3=CC=CC=C3)O)O

Technology Process of (3aR,4R,5R,6R,6aS)-2-(dimethylamino)-6-(phenylmethoxymethyl)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]oxazole-4,5-diol

There total 42 articles about (3aR,4R,5R,6R,6aS)-2-(dimethylamino)-6-(phenylmethoxymethyl)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]oxazole-4,5-diol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

(1S,5S)-6-exo,7-endo-dibenzoyloxy-8-exo-benzyloxymethyl-3-dimethylamino-2-oxa-4-azabicyclo<3.3.0>octan-3-ene (165375-31-5) → (1S,5R)-8-exo-benzyloxymethyl-3-dimethylamino-6-exo,7-endo-dihydroxy-2-oxa-4-azabicyclo<3.3.0>octan-3-ene (124583-64-8,124648-52-8,124648-53-9,124648-54-0,134875-86-8)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 16h;

Reference yield: 90.0%

6-O-benzyl-4-O-(tert-butyldimethysilyl)-(-)-allosamizoline (174810-42-5) → (1S,5R)-8-exo-benzyloxymethyl-3-dimethylamino-6-exo,7-endo-dihydroxy-2-oxa-4-azabicyclo<3.3.0>octan-3-ene (124583-64-8,124648-52-8,124648-53-9,124648-54-0,134875-86-8)

Guidance literature:

With hydrogen fluoride; In acetonitrile; for 18h; Ambient temperature;

DOI:10.1016/0040-4039(95)02230-9

Reference yield: 81.6%

(+/-)-4S-<(benzyloxy)methyl>-2-(N,N-dimethylamino)cyclopent-5-eno<4,5-d>-3aS,6aR-oxzoline (124583-61-5,134875-87-9) → (+/-)-4S-<(benzyloxy)methyl>-2-(dimethylamino)-5S,6R-dihydroxycyclopentano<4,3-d>-3aS,6aS-oxazoline (124583-64-8,124648-52-8,124648-53-9,124648-54-0,134875-86-8)

Guidance literature:

With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In tetrahydrofuran; water; for 26h; Ambient temperature;

DOI:10.1021/ja00055a013

upstream raw materials:

(+/-)-4S-<(benzyloxy)methyl>-2-(N,N-dimethylamino)cyclopent-5-eno<4,5-d>-3aS,6aR-oxzoline

(1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol

(+/-)-4S-<(benzyloxy)methyl>cyclopent-5-eno<4,5-d>-3aR,6aS-oxazolidin-2-one

(+/-)-4S-<(benzyloxy)methyl>-1-<(4'-methylphenyl)sulfonyl>cyclopent-5-eno<4,5-d>-3aR,6aS-1,3-oxazolidinone

Downstream raw materials:

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-((3aR,4R,5R,6S,6aS)-6-benzyloxymethyl-2-dimethylamino-4-hydroxy-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-yloxy)-tetrahydro-pyran-4-yl ester

(3aR,4S,5S,6R,6aR)-4-Acetoxy-6-<(benzyloxy)methyl>-2-(dimethylamino)-3a,5,6,6a-tetrahydro-4H-cyclopentoxazol-5-yl 2-acetamido-4-O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-allopyranosyl)-3,6-di-O-benzyl-2-deoxy-β-D-allopyranoside

(3aS,4S,5S,6R,6aR)-6-<(Benzyloxy)methyl>-2-(dimethylamino)-3a,5,6,6a-tetrahydro-4-hydroxy-4H-cyclopentoxazol-5-yl 2-acetamido-4-O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-allopyranosyl)-3,6-di-O-benzyl-2-deoxy-β-D-allopyranoside

Isoallosamidin

Refernces

• 1、 Shrader, William D.,Imperiali, Barbara. "Synthesis of the glucoallosamidin pseudo-disaccharide: Use of an efficient Hg(II) mediated cyclization". . p. 599 - 602. Retrieved 2007/10/02.
• 2、 Blattner, Regine,Furneaux, Richard H.,Kemmitt, timothy,Tyler, Peter C.,Ferrier, Robert J.,Tiden, Anna-Karin. "Syntheses of the Fungicide/Insecticide Allosamidin and a Structural Isomer". . p. 3411 - 3422. Retrieved 2007/10/02.