(3aR,4R,6R,6aS)-Tetrahydro-2,2-dimethyl-6-(benzyloxyamino)-4H-cyclopenta-1,3-dioxol-4-ol

Base Information

• Chemical Name: (3aR,4R,6R,6aS)-Tetrahydro-2,2-dimethyl-6-(benzyloxyamino)-4H-cyclopenta-1,3-dioxol-4-ol
• CAS No.: 138946-55-1
• Molecular Formula: C₁₅H₂₁NO₄
• Molecular Weight: 279.336
• DSSTox Substance ID: DTXSID301118100
• Nikkaji Number: J876.512J
• Mol file: 138946-55-1.mol

Synonyms:DTXSID301118100;(3aR,4R,6R,6aS)-Tetrahydro-2,2-dimethyl-6-(benzyloxyamino)-4H-cyclopenta-1,3-dioxol-4-ol;(3aR,4R,6R,6aS)-Tetrahydro-2,2-dimethyl-6-[(phenylmethoxy)amino]-4H-cyclopenta-1,3-dioxol-4-ol;138946-55-1

Chemical Property of (3aR,4R,6R,6aS)-Tetrahydro-2,2-dimethyl-6-(benzyloxyamino)-4H-cyclopenta-1,3-dioxol-4-ol

Chemical Property:

• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 279.14705815
• Heavy Atom Count: 20
• Complexity: 330

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(OC2C(CC(C2O1)O)NOCC3=CC=CC=C3)C
• Isomeric SMILES: CC1(O[C@H]2[C@@H](C[C@H]([C@H]2O1)O)NOCC3=CC=CC=C3)C

Technology Process of (3aR,4R,6R,6aS)-Tetrahydro-2,2-dimethyl-6-(benzyloxyamino)-4H-cyclopenta-1,3-dioxol-4-ol

There total 12 articles about (3aR,4R,6R,6aS)-Tetrahydro-2,2-dimethyl-6-(benzyloxyamino)-4H-cyclopenta-1,3-dioxol-4-ol 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: 79.0%

5-bromo-2,3-O-isopropylidene-2,3,4-trihydroxypentanal-O-benzyl oxime (138946-45-9,138946-46-0) → (1R,2R,3S,4R)-4-(benzyloxyamino)-2,3-O-isopropylidenecyclopentane-1,2,3-triol (138946-55-1)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; at 80 ℃;

DOI:10.1039/c39940000083

Reference yield: 75.0%

5-deoxy-5-iodo-2,3-O-isopropylidene-D-ribose O-benzyl oxime ether → (1R,2R,3S,4R)-4-(benzyloxyamino)-2,3-O-isopropylidenecyclopentane-1,2,3-triol (138946-55-1)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 0.5h; Heating;

DOI:10.1016/S0957-4166(97)00236-X

Reference yield: 42.0%

Benzoic acid (3aR,4R,6aS)-6-benzyloxyamino-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl ester → (1R,2R,3S,4R)-4-(benzyloxyamino)-2,3-O-isopropylidenecyclopentane-1,2,3-triol (138946-55-1)

Guidance literature:

With sodium methylate; In methanol; for 2h; Ambient temperature;

DOI:10.1021/jo970987w

upstream raw materials:

5-bromo-2,3-O-isopropylidene-2,3,4-trihydroxypentanal-O-benzyl oxime

2,3-O-isopropylidene-D-ribonic-γ-lactone

5-bromo-5-deoxy-2,3-O-isopropylidene-D-ribono-1,4-lactone

(4R,5R)-5-((S)-2-Bromo-1-hydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

Downstream raw materials:

(1R,2R,3S,4R)-4-Benzyloxyamino-cyclopentane-1,2,3-triol

(1S,2S,3R,5S)-4-O-benzylhydroxylamino-5-iodo-2,3-O-isopropylidene-1,2-cyclopentanediol

(3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol