(3aS,3bS,6aR,7R,7aS)-7-Benzyloxymethyl-7-iodo-6-(4-methoxy-benzyl)-2,2-dimethyl-hexahydro-1,3,4-trioxa-6-aza-cyclopenta[a]pentalen-5-one

Base Information

• Chemical Name: (3aS,3bS,6aR,7R,7aS)-7-Benzyloxymethyl-7-iodo-6-(4-methoxy-benzyl)-2,2-dimethyl-hexahydro-1,3,4-trioxa-6-aza-cyclopenta[a]pentalen-5-one
• CAS No.: 158631-97-1
• Molecular Formula: C₂₅H₂₈INO₆
• Molecular Weight: 565.405
• Mol file: 158631-97-1.mol

Synonyms:(3aS,3bS,6aR,7R,7aS)-7-Benzyloxymethyl-7-iodo-6-(4-methoxy-benzyl)-2,2-dimethyl-hexahydro-1,3,4-trioxa-6-aza-cyclopenta[a]pentalen-5-one

Chemical Property of (3aS,3bS,6aR,7R,7aS)-7-Benzyloxymethyl-7-iodo-6-(4-methoxy-benzyl)-2,2-dimethyl-hexahydro-1,3,4-trioxa-6-aza-cyclopenta[a]pentalen-5-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,3bS,6aR,7R,7aS)-7-Benzyloxymethyl-7-iodo-6-(4-methoxy-benzyl)-2,2-dimethyl-hexahydro-1,3,4-trioxa-6-aza-cyclopenta[a]pentalen-5-one

There total 1 articles about (3aS,3bS,6aR,7R,7aS)-7-Benzyloxymethyl-7-iodo-6-(4-methoxy-benzyl)-2,2-dimethyl-hexahydro-1,3,4-trioxa-6-aza-cyclopenta[a]pentalen-5-one 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:

1-(isothiocyanatomethyl)-4-methoxybenzene (3694-57-3) + (1S,4R,5S)-(-)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-ol (89291-76-9) → (3aS,3bS,6aR,7R,7aS)-7-Benzyloxymethyl-7-iodo-6-(4-methoxy-benzyl)-2,2-dimethyl-hexahydro-1,3,4-trioxa-6-aza-cyclopenta[a]pentalen-5-one (158631-97-1)

Guidance literature:

With iodine; sodium hydride; sodium carbonate; sodium sulfite; methyl iodide; Yield given. Multistep reaction; 2.) THF;

Reference yield:

(3aS,3bS,6aR,7R,7aS)-7-Benzyloxymethyl-7-iodo-6-(4-methoxy-benzyl)-2,2-dimethyl-hexahydro-1,3,4-trioxa-6-aza-cyclopenta[a]pentalen-5-one (158631-97-1) → (3aR,4R,5S,6R,6aS)-4,5,6-Tris-benzyloxy-4-benzyloxymethyl-3-(4-methoxy-benzyl)-hexahydro-cyclopentaoxazol-2-one

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) H₂SO₄, 2.) Zn / 2.) THF

2: K₂CO₃ / methanol; H₂O

3: DEAD, Ph₃P / toluene

4: Na₂CO₃, H₂O / methanol

5: 90 percent / CF₃CO₃H, Na₂CO₃ / CH₂Cl₂ / -20 °C

6: 89 percent / PhCO₂Na, H₂O / dimethylformamide / 12 h / 100 °C

7: NaH, n-Bu₄NI / tetrahydrofuran

With sodium benzoate; trifluoroacetyl peroxide; sulfuric acid; water; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium carbonate; potassium carbonate; triphenylphosphine; zinc; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

Reference yield:

(3aS,3bS,6aR,7R,7aS)-7-Benzyloxymethyl-7-iodo-6-(4-methoxy-benzyl)-2,2-dimethyl-hexahydro-1,3,4-trioxa-6-aza-cyclopenta[a]pentalen-5-one (158631-97-1) → (1aR,1bR,4aS,5R,5aR)-1a-Benzyloxymethyl-5-hydroxy-2-(4-methoxy-benzyl)-hexahydro-1,4-dioxa-2-aza-cyclopropa[a]pentalen-3-one (158632-00-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) H₂SO₄, 2.) Zn / 2.) THF

2: K₂CO₃ / methanol; H₂O

3: DEAD, Ph₃P / toluene

4: Na₂CO₃, H₂O / methanol

5: 90 percent / CF₃CO₃H, Na₂CO₃ / CH₂Cl₂ / -20 °C

With trifluoroacetyl peroxide; sulfuric acid; water; sodium carbonate; potassium carbonate; triphenylphosphine; zinc; diethylazodicarboxylate; In methanol; dichloromethane; water; toluene;

upstream raw materials:

1-(isothiocyanatomethyl)-4-methoxybenzene

(1S,4R,5S)-(-)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-ol

Downstream raw materials:

Acetic acid (3aS,6R,6aS)-4-benzyloxymethyl-3-(4-methoxy-benzyl)-2-oxo-3,3a,6,6a-tetrahydro-2H-cyclopentaoxazol-6-yl ester

(1aR,1bR,4aS,5R,5aR)-1a-Benzyloxymethyl-5-hydroxy-2-(4-methoxy-benzyl)-hexahydro-1,4-dioxa-2-aza-cyclopropa[a]pentalen-3-one

(3aR,4R,5S,6S,6aS)-4-Benzyloxymethyl-4,5,6-trihydroxy-3-(4-methoxy-benzyl)-hexahydro-cyclopentaoxazol-2-one

(1S,2R,3R,4S,5R)-2-Amino-3,4,5-tris-benzyloxy-3-benzyloxymethyl-cyclopentanol