<3aS)-(3aα,4α,7aα,7α)>-1-oxy>ethyl>-1,3-dioxolo<4,5-c>pyran-7-yl>-3-pentyn-2-one

Base Information

Chemical Name:<3aS)-(3aα,4α,7aα,7α)>-1-oxy>ethyl>-1,3-dioxolo<4,5-c>pyran-7-yl>-3-pentyn-2-one
CAS No.:107148-29-8
Molecular Formula:C₃₁H₄₀O₅Si
Molecular Weight:520.741
Hs Code.:

<3aS)-(3aα,4α,7aα,7α)>-1-<tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-1,3-dioxolo<4,5-c>pyran-7-yl>-3-pentyn-2-one

Synonyms:<3aS)-(3aα,4α,7aα,7α)>-1-oxy>ethyl>-1,3-dioxolo<4,5-c>pyran-7-yl>-3-pentyn-2-one

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Chemical Property of <3aS)-(3aα,4α,7aα,7α)>-1-oxy>ethyl>-1,3-dioxolo<4,5-c>pyran-7-yl>-3-pentyn-2-one

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Technology Process of <3aS)-(3aα,4α,7aα,7α)>-1-oxy>ethyl>-1,3-dioxolo<4,5-c>pyran-7-yl>-3-pentyn-2-one

There total 13 articles about <3aS)-(3aα,4α,7aα,7α)>-1-oxy>ethyl>-1,3-dioxolo<4,5-c>pyran-7-yl>-3-pentyn-2-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: 96.0%

: 4529-04-8
1-propynyl lithium

: 107148-24-3
<3aR-(3aα,4α,7α,7aα)>-tetrahydro-N,N,2,2-tetramethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-4H-1,3-dioxolo<4,5-c>pyran-7-acetamide

: 107148-29-8
<3aS)-(3aα,4α,7aα,7α)>-1-oxy>ethyl>-1,3-dioxolo<4,5-c>pyran-7-yl>-3-pentyn-2-one

Guidance literature:: With boron trifluoride diethyl etherate; In tetrahydrofuran; at -78 ℃;
DOI:10.1021/jo00383a046

Reference yield:

: 107148-23-2
(5S-cis)-5,6-dihydro-6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2H-pyran-5-ol

: 107148-29-8
<3aS)-(3aα,4α,7aα,7α)>-1-oxy>ethyl>-1,3-dioxolo<4,5-c>pyran-7-yl>-3-pentyn-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: 95 percent / xylene

2: 90 percent / OsO₄, NMO

3: 90 percent / p-TsOH

4: 96 percent / BF₃*Et₂O / tetrahydrofuran / -78 °C

With osmium(VIII) oxide; N-methyl-2-indolinone; boron trifluoride diethyl etherate; toluene-4-sulfonic acid; In tetrahydrofuran; xylene;
DOI:10.1021/jo00383a046

Reference yield:

: (2S,3S)-2-(2-Hydroxy-ethyl)-3,6-dihydro-2H-pyran-3-ol

: 107148-29-8
<3aS)-(3aα,4α,7aα,7α)>-1-oxy>ethyl>-1,3-dioxolo<4,5-c>pyran-7-yl>-3-pentyn-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: pyridine / 2 h / 0 - 20 °C

2: 100 percent / xylene / 12 h / Heating

3: 90 percent / N-methylmorpholine N-oxide, OsO₄ / acetone; H₂O / 24 h / Ambient temperature

4: 94 percent / cupric sulfate, p-toluenesulfonic acid / 24 h / Ambient temperature

5: 1.) n-BuLi, BF₃ / 1.) THF, hexane, ether, -78 deg C, 20 min, 2.) 30 min

With pyridine; osmium(VIII) oxide; n-butyllithium; boron trifluoride; toluene-4-sulfonic acid; copper(II) sulfate; 4-methylmorpholine N-oxide; In water; acetone; xylene;
DOI:10.1021/jo00253a021