(3S,5R)-3-[3-(benzyloxy)propyl]-5-hydroxy-14-methoxy-3,4,5,6,7,8-hexahydro-1H-2-benzoxacyclododecin-1-one

Base Information

Chemical Name:(3S,5R)-3-[3-(benzyloxy)propyl]-5-hydroxy-14-methoxy-3,4,5,6,7,8-hexahydro-1H-2-benzoxacyclododecin-1-one
CAS No.:404936-52-3
Molecular Formula:C₂₆H₃₂O₅
Molecular Weight:424.537
Hs Code.:

Synonyms:(3S,5R)-3-[3-(benzyloxy)propyl]-5-hydroxy-14-methoxy-3,4,5,6,7,8-hexahydro-1H-2-benzoxacyclododecin-1-one

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Chemical Property of (3S,5R)-3-[3-(benzyloxy)propyl]-5-hydroxy-14-methoxy-3,4,5,6,7,8-hexahydro-1H-2-benzoxacyclododecin-1-one

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Technology Process of (3S,5R)-3-[3-(benzyloxy)propyl]-5-hydroxy-14-methoxy-3,4,5,6,7,8-hexahydro-1H-2-benzoxacyclododecin-1-one

There total 22 articles about (3S,5R)-3-[3-(benzyloxy)propyl]-5-hydroxy-14-methoxy-3,4,5,6,7,8-hexahydro-1H-2-benzoxacyclododecin-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: 50.0%

: 404936-51-2
2-[(1E,6R,8S)-11-(benzyloxy)-6,8-dihydroxy-1-undecenyl]-6-methoxybenzoic acid

: 404936-52-3
(3S,5R)-3-[3-(benzyloxy)propyl]-5-hydroxy-14-methoxy-3,4,5,6,7,8-hexahydro-1H-2-benzoxacyclododecin-1-one

Guidance literature:: With dmap; 2,4,6-trichlorobenzoyl chloride; triethylamine; In toluene; for 18h; Heating;
DOI:10.1021/ol017261d

Reference yield: 50.0%

: 4136-95-2
2,4,6-trichlorobenzoyl chloride

: 404936-51-2
2-[(1E,6R,8S)-11-(benzyloxy)-6,8-dihydroxy-1-undecenyl]-6-methoxybenzoic acid

: 404936-52-3
(3S,5R)-3-[3-(benzyloxy)propyl]-5-hydroxy-14-methoxy-3,4,5,6,7,8-hexahydro-1H-2-benzoxacyclododecin-1-one

: (3S,5R)-3-[3-(benzyloxy)propyl]-14-methoxy-1-oxo-3,4,5,6,7,8-hexahydro-1H-2-benzoxacyclododecin-5-yl 2,4,6-trichlorobenzoate

Guidance literature:: 2,4,6-trichlorobenzoyl chloride; 2-[(1E,6R,8S)-11-(benzyloxy)-6,8-dihydroxy-1-undecenyl]-6-methoxybenzoic acid; With triethylamine; In tetrahydrofuran; for 2h; Heating;

With dmap; In tetrahydrofuran; toluene; for 16h;

Reference yield:

: 145645-18-7
methyl 2-methoxy-6-{[(trifluoromethyl)sulfonyl]oxy}benzoate

: 404936-52-3
(3S,5R)-3-[3-(benzyloxy)propyl]-5-hydroxy-14-methoxy-3,4,5,6,7,8-hexahydro-1H-2-benzoxacyclododecin-1-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 85 percent / P(2-furyl)3; NMP; LiCl / [Pd₂(dba)3]

2.1: 99 percent / aq. LiOH / methanol

3.1: Et₃N / tetrahydrofuran / 2 h / Heating

3.2: 50 percent / DMAP / tetrahydrofuran; toluene / 16 h

With 1-methyl-pyrrolidin-2-one; lithium hydroxide; trifuran-2-yl-phosphane; triethylamine; lithium chloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In tetrahydrofuran; methanol;