(4aR,5aS,9R,10aS,11R,11aR)-11-Benzyloxymethoxy-9-((E)-(S)-3,4-bis-benzyloxymethoxy-but-1-enyl)-2,2-dimethyl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene

Base Information

• Chemical Name: (4aR,5aS,9R,10aS,11R,11aR)-11-Benzyloxymethoxy-9-((E)-(S)-3,4-bis-benzyloxymethoxy-but-1-enyl)-2,2-dimethyl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene
• CAS No.: 173613-41-7
• Molecular Formula: C₄₁H₅₀O₁₀
• Molecular Weight: 702.842
• Mol file: 173613-41-7.mol

Synonyms:

Chemical Property of (4aR,5aS,9R,10aS,11R,11aR)-11-Benzyloxymethoxy-9-((E)-(S)-3,4-bis-benzyloxymethoxy-but-1-enyl)-2,2-dimethyl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aR,5aS,9R,10aS,11R,11aR)-11-Benzyloxymethoxy-9-((E)-(S)-3,4-bis-benzyloxymethoxy-but-1-enyl)-2,2-dimethyl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene

There total 13 articles about (4aR,5aS,9R,10aS,11R,11aR)-11-Benzyloxymethoxy-9-((E)-(S)-3,4-bis-benzyloxymethoxy-but-1-enyl)-2,2-dimethyl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene 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: 46.0%

Benzyloxymethyl chloride (3587-60-8) + (E)-(S)-4-((4aR,5aS,9R,10aR,11R,11aS)-11-Hydroxy-2,2-dimethyl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-9-yl)-but-3-ene-1,2-diol (173613-37-1) → (4aR,5aS,9R,10aS,11R,11aR)-11-Benzyloxymethoxy-9-((E)-(S)-3,4-bis-benzyloxymethoxy-but-1-enyl)-2,2-dimethyl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene (173613-41-7)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; In dichloromethane; for 15h; Ambient temperature;

DOI:10.1016/S0040-4020(97)00071-9

Reference yield:

4-Bromo-benzoic acid (4aR,5aS,9R,10aS,11R,11aR)-9-formyl-2,2-dimethyl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-11-yl ester → (4aR,5aS,9R,10aS,11R,11aR)-11-Benzyloxymethoxy-9-((E)-(S)-3,4-bis-benzyloxymethoxy-but-1-enyl)-2,2-dimethyl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene (173613-41-7)

Guidance literature:

Multi-step reaction with 7 steps

1: benzene / 1.5 h / Ambient temperature

2: CeCl₃*7H₂O, NaBH₄ / methanol / 1 h / -60 °C

3: 93 percent / Et₃N, DMAP / CH₂Cl₂ / 1.5 h / Ambient temperature

4: 89 percent / DDQ / CH₂Cl₂ / 3 h / Ambient temperature

5: Et₃N, DMAP / CH₂Cl₂ / 2 h / Ambient temperature

6: 0.3 mg / K₂CO₃ / methanol / 27 h / Ambient temperature

7: 46 percent / (iPr)2NEt, Bu₄NI / CH₂Cl₂ / 15 h / Ambient temperature

With dmap; sodium tetrahydroborate; cerium(III) chloride; tetra-(n-butyl)ammonium iodide; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane; benzene;

DOI:10.1016/S0040-4020(97)00071-9

Reference yield:

4-Bromo-benzoic acid (4aR,5aS,9R,10aS,11R,11aR)-9-hydroxymethyl-2,2-dimethyl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-11-yl ester (173613-34-8) → (4aR,5aS,9R,10aS,11R,11aR)-11-Benzyloxymethoxy-9-((E)-(S)-3,4-bis-benzyloxymethoxy-but-1-enyl)-2,2-dimethyl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene (173613-41-7)

Guidance literature:

Multi-step reaction with 8 steps

1: Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / Ambient temperature

2: benzene / 1.5 h / Ambient temperature

3: CeCl₃*7H₂O, NaBH₄ / methanol / 1 h / -60 °C

4: 93 percent / Et₃N, DMAP / CH₂Cl₂ / 1.5 h / Ambient temperature

5: 89 percent / DDQ / CH₂Cl₂ / 3 h / Ambient temperature

6: Et₃N, DMAP / CH₂Cl₂ / 2 h / Ambient temperature

7: 0.3 mg / K₂CO₃ / methanol / 27 h / Ambient temperature

8: 46 percent / (iPr)2NEt, Bu₄NI / CH₂Cl₂ / 15 h / Ambient temperature

With dmap; sodium tetrahydroborate; cerium(III) chloride; tetra-(n-butyl)ammonium iodide; potassium carbonate; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane; benzene;

DOI:10.1016/S0040-4020(97)00071-9

upstream raw materials:

Benzyloxymethyl chloride

(E)-(S)-4-((4aR,5aS,9R,10aR,11R,11aS)-11-Hydroxy-2,2-dimethyl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-9-yl)-but-3-ene-1,2-diol

4-Bromo-benzoic acid (4aR,5aS,9R,10aS,11R,11aR)-9-hydroxymethyl-2,2-dimethyl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-11-yl ester

4-Bromo-benzoic acid (4aR,5aS,8R,9S,10aS,11R,11aR)-8-hydroxy-2,2-dimethyl-9-vinyl-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-11-yl ester

Downstream raw materials:

(S)-2,3-Bis-benzyloxymethoxy-propan-1-ol