(3R,3aR,11aR)-3-((S)-2-Benzyloxymethoxy-1-hydroxy-ethyl)-3a,5,10,11a-tetrahydro-3H-2,4,11-trioxa-benzo[a]cyclopenta[e]cycloocten-1-one

Base Information

Chemical Name:(3R,3aR,11aR)-3-((S)-2-Benzyloxymethoxy-1-hydroxy-ethyl)-3a,5,10,11a-tetrahydro-3H-2,4,11-trioxa-benzo[a]cyclopenta[e]cycloocten-1-one
CAS No.:127940-44-7
Molecular Formula:C₂₂H₂₄O₇
Molecular Weight:400.428
Hs Code.:

Synonyms:(3R,3aR,11aR)-3-((S)-2-Benzyloxymethoxy-1-hydroxy-ethyl)-3a,5,10,11a-tetrahydro-3H-2,4,11-trioxa-benzo[a]cyclopenta[e]cycloocten-1-one

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Chemical Property of (3R,3aR,11aR)-3-((S)-2-Benzyloxymethoxy-1-hydroxy-ethyl)-3a,5,10,11a-tetrahydro-3H-2,4,11-trioxa-benzo[a]cyclopenta[e]cycloocten-1-one

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Technology Process of (3R,3aR,11aR)-3-((S)-2-Benzyloxymethoxy-1-hydroxy-ethyl)-3a,5,10,11a-tetrahydro-3H-2,4,11-trioxa-benzo[a]cyclopenta[e]cycloocten-1-one

There total 5 articles about (3R,3aR,11aR)-3-((S)-2-Benzyloxymethoxy-1-hydroxy-ethyl)-3a,5,10,11a-tetrahydro-3H-2,4,11-trioxa-benzo[a]cyclopenta[e]cycloocten-1-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: 90.0%

: 128995-28-8
(R)-3-((S)-2-Benzyloxymethoxy-1-hydroxy-ethyl)-5,10-dihydro-3H-2,4,11-trioxa-benzo[a]cyclopenta[e]cycloocten-1-one

: 127940-44-7
(3R,3aR,11aR)-3-((S)-2-Benzyloxymethoxy-1-hydroxy-ethyl)-3a,5,10,11a-tetrahydro-3H-2,4,11-trioxa-benzo[a]cyclopenta[e]cycloocten-1-one

Guidance literature:: With Rh(Diphos-4)(NBD)BF₄; hydrogen; In dichloromethane; for 20h; under 100844 Torr; Ambient temperature;
DOI:10.1016/S0040-4039(01)93741-4

Reference yield:

: 612-12-4
o-Xylylene dichloride

: 127940-44-7
(3R,3aR,11aR)-3-((S)-2-Benzyloxymethoxy-1-hydroxy-ethyl)-3a,5,10,11a-tetrahydro-3H-2,4,11-trioxa-benzo[a]cyclopenta[e]cycloocten-1-one

Guidance literature:: Multi-step reaction with 4 steps

1: 62 percent / K₂CO₃ / dimethylformamide / 2.5 h / 60 °C

2: 99 percent / 1 M HCl / methanol / 12 h / Ambient temperature

3: 57 percent / i-Pr₂NEt / CH₂Cl₂ / 48 h / Ambient temperature

4: 90 percent / Rh(Diphos-4)(NBD)BF₄, H₂ / CH₂Cl₂ / 20 h / 100844 Torr / Ambient temperature

With hydrogenchloride; Rh(Diphos-4)(NBD)BF₄; hydrogen; potassium carbonate; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(01)93741-4

Reference yield:

: 127940-45-8
(R)-3-((S)-1,2-Dihydroxy-ethyl)-5,10-dihydro-3H-2,4,11-trioxa-benzo[a]cyclopenta[e]cycloocten-1-one

: 127940-44-7
(3R,3aR,11aR)-3-((S)-2-Benzyloxymethoxy-1-hydroxy-ethyl)-3a,5,10,11a-tetrahydro-3H-2,4,11-trioxa-benzo[a]cyclopenta[e]cycloocten-1-one

Guidance literature:: Multi-step reaction with 2 steps

1: 57 percent / i-Pr₂NEt / CH₂Cl₂ / 48 h / Ambient temperature

2: 90 percent / Rh(Diphos-4)(NBD)BF₄, H₂ / CH₂Cl₂ / 20 h / 100844 Torr / Ambient temperature

With Rh(Diphos-4)(NBD)BF₄; hydrogen; N-ethyl-N,N-diisopropylamine; In dichloromethane;
DOI:10.1016/S0040-4039(01)93741-4