(4R,6R)-4-(dimethylphenylsilyl)-6-{[(6S)-4-(dimethylphenylsilyl)-2,2-dioxo-1,2-oxathian-6-yl]methyl}-3,4,5,6-tetrahydro-2H-pyran-2-one

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Chemical Name:(4R,6R)-4-(dimethylphenylsilyl)-6-{[(6S)-4-(dimethylphenylsilyl)-2,2-dioxo-1,2-oxathian-6-yl]methyl}-3,4,5,6-tetrahydro-2H-pyran-2-one
CAS No.:1643685-75-9
Molecular Formula:C₂₆H₃₆O₅SSi₂
Molecular Weight:516.806
Hs Code.:

Synonyms:(4R,6R)-4-(dimethylphenylsilyl)-6-{[(6S)-4-(dimethylphenylsilyl)-2,2-dioxo-1,2-oxathian-6-yl]methyl}-3,4,5,6-tetrahydro-2H-pyran-2-one

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Chemical Property of (4R,6R)-4-(dimethylphenylsilyl)-6-{[(6S)-4-(dimethylphenylsilyl)-2,2-dioxo-1,2-oxathian-6-yl]methyl}-3,4,5,6-tetrahydro-2H-pyran-2-one

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Technology Process of (4R,6R)-4-(dimethylphenylsilyl)-6-{[(6S)-4-(dimethylphenylsilyl)-2,2-dioxo-1,2-oxathian-6-yl]methyl}-3,4,5,6-tetrahydro-2H-pyran-2-one

There total 7 articles about (4R,6R)-4-(dimethylphenylsilyl)-6-{[(6S)-4-(dimethylphenylsilyl)-2,2-dioxo-1,2-oxathian-6-yl]methyl}-3,4,5,6-tetrahydro-2H-pyran-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:

: 1643685-72-6
(S)-6-{[(R)-2,2-dioxo-5,6-dihydro-1,2-oxathiin-6-yl]methyl}-5,6-dihydro-2H-pyran-2-one

: 768-33-2
phenyldimethylsilyl chloride

: 1643685-75-9
(4R,6R)-4-(dimethylphenylsilyl)-6-{[(6S)-4-(dimethylphenylsilyl)-2,2-dioxo-1,2-oxathian-6-yl]methyl}-3,4,5,6-tetrahydro-2H-pyran-2-one

: 1643685-89-5
(4R,6R)-4-(dimethylphenylsilyl)-6-{[(6S)-4-(dimethylphenylsilyl)-2,2-dioxo-1,2-oxathian-6-yl]methyl}-3,4,5,6-tetrahydro-2H-pyran-2-one

Guidance literature:: phenyldimethylsilyl chloride; With lithium; In tetrahydrofuran; at -10 ℃; for 18h; Inert atmosphere;

(S)-6-{[(R)-2,2-dioxo-5,6-dihydro-1,2-oxathiin-6-yl]methyl}-5,6-dihydro-2H-pyran-2-one; With copper(l) cyanide; In tetrahydrofuran; at -78 - -50 ℃; for 3h; Overall yield = 88 %; Overall yield = 1.69 g; Optical yield = 36 %de; Inert atmosphere;
DOI:10.1002/ejoc.201400145

Reference yield:

: 1643685-69-1
(4S,6R)-6-[(ethenesulfonyl)oxy]nona-1,8-dien-4-yl (E)-but-2-enoate

: 1643685-75-9
(4R,6R)-4-(dimethylphenylsilyl)-6-{[(6S)-4-(dimethylphenylsilyl)-2,2-dioxo-1,2-oxathian-6-yl]methyl}-3,4,5,6-tetrahydro-2H-pyran-2-one

: 1643685-89-5
(4R,6R)-4-(dimethylphenylsilyl)-6-{[(6S)-4-(dimethylphenylsilyl)-2,2-dioxo-1,2-oxathian-6-yl]methyl}-3,4,5,6-tetrahydro-2H-pyran-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: Schwartz's reagent / toluene / 3 h / 100 °C / Inert atmosphere

2.1: lithium / tetrahydrofuran / 18 h / -10 °C / Inert atmosphere

2.2: 3 h / -78 - -50 °C / Inert atmosphere

With Schwartz's reagent; lithium; In tetrahydrofuran; toluene;
DOI:10.1002/ejoc.201400145

Reference yield:

: (4R,6R)-nona-1,8-diene-4,6-diol

: 1643685-75-9
(4R,6R)-4-(dimethylphenylsilyl)-6-{[(6S)-4-(dimethylphenylsilyl)-2,2-dioxo-1,2-oxathian-6-yl]methyl}-3,4,5,6-tetrahydro-2H-pyran-2-one

: 1643685-89-5
(4R,6R)-4-(dimethylphenylsilyl)-6-{[(6S)-4-(dimethylphenylsilyl)-2,2-dioxo-1,2-oxathian-6-yl]methyl}-3,4,5,6-tetrahydro-2H-pyran-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: triphenylphosphine; di-isopropyl azodicarboxylate / toluene / -30 - 20 °C / Inert atmosphere

2.1: triethylamine / tetrahydrofuran / 0.5 h / 15 °C / Inert atmosphere

3.1: Schwartz's reagent / toluene / 3 h / 100 °C / Inert atmosphere

4.1: lithium / tetrahydrofuran / 18 h / -10 °C / Inert atmosphere

4.2: 3 h / -78 - -50 °C / Inert atmosphere

With Schwartz's reagent; di-isopropyl azodicarboxylate; lithium; triethylamine; triphenylphosphine; In tetrahydrofuran; toluene; 1.1: |Mitsunobu Displacement;
DOI:10.1002/ejoc.201400145