(1S,8S,9S,11S)-1-methoxy-11-(2-methoxybenzyl)oxy-10-oxabicyclo<7.2.1>dodec-4-ene-2,6-diyn-8-ol

Base Information

Chemical Name:(1S,8S,9S,11S)-1-methoxy-11-(2-methoxybenzyl)oxy-10-oxabicyclo<7.2.1>dodec-4-ene-2,6-diyn-8-ol
CAS No.:156161-80-7
Molecular Formula:C₂₀H₂₀O₅
Molecular Weight:340.376
Hs Code.:

Synonyms:(1S,8S,9S,11S)-1-methoxy-11-(2-methoxybenzyl)oxy-10-oxabicyclo<7.2.1>dodec-4-ene-2,6-diyn-8-ol

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Chemical Property of (1S,8S,9S,11S)-1-methoxy-11-(2-methoxybenzyl)oxy-10-oxabicyclo<7.2.1>dodec-4-ene-2,6-diyn-8-ol

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Technology Process of (1S,8S,9S,11S)-1-methoxy-11-(2-methoxybenzyl)oxy-10-oxabicyclo<7.2.1>dodec-4-ene-2,6-diyn-8-ol

There total 14 articles about (1S,8S,9S,11S)-1-methoxy-11-(2-methoxybenzyl)oxy-10-oxabicyclo<7.2.1>dodec-4-ene-2,6-diyn-8-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: 44.0%

: ortho-methoxybenzyl-3-deoxy-2-C-(6-iodo-3-hexene-1,5-diynyl)-2-O-methyl-α-D-erythro-pentodialdo-1,4-furanoside

: 156161-80-7
(1S,8S,9S,11S)-1-methoxy-11-(2-methoxybenzyl)oxy-10-oxabicyclo<7.2.1>dodec-4-ene-2,6-diyn-8-ol

Guidance literature:: With chromium dichloride; nickel dichloride; In tetrahydrofuran; at 23 ℃; for 3.66667h;
DOI:10.1016/S0040-4020(01)80628-1

Reference yield:

: 53081-35-9
methyl 3-deoxy-α-D-threo-pentofuranoside

: 156161-80-7
(1S,8S,9S,11S)-1-methoxy-11-(2-methoxybenzyl)oxy-10-oxabicyclo<7.2.1>dodec-4-ene-2,6-diyn-8-ol

Guidance literature:: Multi-step reaction with 12 steps

1: 84 percent / conc. H₂SO₄ / Ambient temperature

2: 1.) 4 Angstroem MS, 2.) trimethylsilyl triflate / 1.) CH₂Cl₂, r.t., 1.5 h, 2.) CH₂Cl₂, -5 deg C, 2 h

3: 96 percent / 1M NaOMe / methanol / 14 h

4: 84 percent / pyridine / 96 h / 4 °C

5: 91 percent / Dess-Martin-periodinane / CH₂Cl₂ / 1 h

6: 1.) n-BuLi, ceric(III) chloride / 1.) THF, -80 deg C, 1.5 h, 2.) THF, -80 deg C, 30 min

7: 1.) NaH, 2.) 1,3-dimethyl-2-imidazolidinone, 3.) H₂O / 1.) THF, 0 deg C, 30 min, 2.) THF, 0 deg C to r.t., 2 h, 3) THF, 4.5 h

8: 76 percent / Pd(PPh₃)4, n-butylamine, CuI / benzene / 17 h

9: 71 percent / 0.3M NaOMe / methanol / 336 h / Ambient temperature

10: 76 percent / I₂, morpholine / benzene / 4 h / 45 - 50 °C

11: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -50 deg C, 1 h, 2.) CH₂Cl₂, -50 deg C to r.t.,

12: 44 percent / CrCl₂, NiCl₂ / tetrahydrofuran / 3.67 h / 23 °C

With morpholine; pyridine; chromium dichloride; 1,3-dimethyl-2-imidazolidinone; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; cerium(III) chloride; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; 4 Angstroem MS; sulfuric acid; water; iodine; sodium methylate; sodium hydride; Dess-Martin periodane; dimethyl sulfoxide; N-butylamine; triethylamine; nickel dichloride; In tetrahydrofuran; methanol; dichloromethane; benzene;
DOI:10.1016/S0040-4020(01)80628-1

Reference yield:

: 612-16-8
(2-methoxyphenyl)methanol

: 156161-80-7
(1S,8S,9S,11S)-1-methoxy-11-(2-methoxybenzyl)oxy-10-oxabicyclo<7.2.1>dodec-4-ene-2,6-diyn-8-ol

Guidance literature:: Multi-step reaction with 11 steps

1: 1.) 4 Angstroem MS, 2.) trimethylsilyl triflate / 1.) CH₂Cl₂, r.t., 1.5 h, 2.) CH₂Cl₂, -5 deg C, 2 h

2: 96 percent / 1M NaOMe / methanol / 14 h

3: 84 percent / pyridine / 96 h / 4 °C

4: 91 percent / Dess-Martin-periodinane / CH₂Cl₂ / 1 h

5: 1.) n-BuLi, ceric(III) chloride / 1.) THF, -80 deg C, 1.5 h, 2.) THF, -80 deg C, 30 min

6: 1.) NaH, 2.) 1,3-dimethyl-2-imidazolidinone, 3.) H₂O / 1.) THF, 0 deg C, 30 min, 2.) THF, 0 deg C to r.t., 2 h, 3) THF, 4.5 h

7: 76 percent / Pd(PPh₃)4, n-butylamine, CuI / benzene / 17 h

8: 71 percent / 0.3M NaOMe / methanol / 336 h / Ambient temperature

9: 76 percent / I₂, morpholine / benzene / 4 h / 45 - 50 °C

10: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -50 deg C, 1 h, 2.) CH₂Cl₂, -50 deg C to r.t.,

11: 44 percent / CrCl₂, NiCl₂ / tetrahydrofuran / 3.67 h / 23 °C

With morpholine; pyridine; chromium dichloride; 1,3-dimethyl-2-imidazolidinone; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; cerium(III) chloride; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; 4 Angstroem MS; water; iodine; sodium methylate; sodium hydride; Dess-Martin periodane; dimethyl sulfoxide; N-butylamine; triethylamine; nickel dichloride; In tetrahydrofuran; methanol; dichloromethane; benzene;
DOI:10.1016/S0040-4020(01)80628-1