(2S,3S,4R,5R,6S,7R)-7-acetoxy-4-benzyloxy-3-tert-butyldimethylsiloxy-8-nonyn-1,2-diol-5,6-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)]

Base Information

Chemical Name:(2S,3S,4R,5R,6S,7R)-7-acetoxy-4-benzyloxy-3-tert-butyldimethylsiloxy-8-nonyn-1,2-diol-5,6-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)]
CAS No.:882523-29-7
Molecular Formula:C₃₂H₅₀O₁₀Si
Molecular Weight:622.828
Hs Code.:

Synonyms:(2S,3S,4R,5R,6S,7R)-7-acetoxy-4-benzyloxy-3-tert-butyldimethylsiloxy-8-nonyn-1,2-diol-5,6-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)]

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Chemical Property of (2S,3S,4R,5R,6S,7R)-7-acetoxy-4-benzyloxy-3-tert-butyldimethylsiloxy-8-nonyn-1,2-diol-5,6-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)]

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Technology Process of (2S,3S,4R,5R,6S,7R)-7-acetoxy-4-benzyloxy-3-tert-butyldimethylsiloxy-8-nonyn-1,2-diol-5,6-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)]

There total 22 articles about (2S,3S,4R,5R,6S,7R)-7-acetoxy-4-benzyloxy-3-tert-butyldimethylsiloxy-8-nonyn-1,2-diol-5,6-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)] 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: 86.1%

: 882523-28-6
(2S,3S,4R,5R,6S,7R)-7-acetoxy-4-benzyloxy-3-tert-butyldimethylsiloxy-1,2-O-isopropylidenedioxy-8-nonyne-5,6-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)]

: 882523-29-7
(2S,3S,4R,5R,6S,7R)-7-acetoxy-4-benzyloxy-3-tert-butyldimethylsiloxy-8-nonyn-1,2-diol-5,6-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)]

Guidance literature:: With silica gel; iron(III) chloride; In chloroform; at 20 ℃; for 2h;
DOI:10.3987/COM-05-S(T)71

Reference yield:

: 100-39-0
benzyl bromide

: 882523-29-7
(2S,3S,4R,5R,6S,7R)-7-acetoxy-4-benzyloxy-3-tert-butyldimethylsiloxy-8-nonyn-1,2-diol-5,6-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)]

Guidance literature:: Multi-step reaction with 6 steps

1.1: 93.8 percent / NaH / dimethylformamide / 0.5 h / 0 °C

2.1: 84.7 percent / TBAF / tetrahydrofuran; hexane / 0.5 h / 0 °C

3.1: 71.5 percent / PCC; NaOAc; Celite / CH₂Cl₂ / 2 h / 20 °C

4.1: n-BuLi / tetrahydrofuran; hexane

4.2: 73.5 percent / tetrahydrofuran; hexane / -78 °C

5.1: NaBH₄ / ethanol; H₂O; tetrahydrofuran / 20 h / 4 °C

5.2: DMAP; pyridine / CH₂Cl₂ / 20 °C

5.3: Et₃N / CH₂Cl₂ / 20 °C

6.1: 86.1 percent / FeCl₃*SiO₂ / CHCl₃ / 2 h / 20 °C

With sodium tetrahydroborate; n-butyllithium; Celite; tetrabutyl ammonium fluoride; sodium acetate; silica gel; iron(III) chloride; sodium hydride; pyridinium chlorochromate; In tetrahydrofuran; ethanol; hexane; dichloromethane; chloroform; water; N,N-dimethyl-formamide;
DOI:10.3987/COM-05-S(T)71

Reference yield:

: 882523-27-5
(2S)-6-hydroxy-2-[(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-4,5-bis(methoxymethyloxymethyl)-6H-pyran-3(2H)-one

: 882523-29-7
(2S,3S,4R,5R,6S,7R)-7-acetoxy-4-benzyloxy-3-tert-butyldimethylsiloxy-8-nonyn-1,2-diol-5,6-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)]

Guidance literature:: Multi-step reaction with 10 steps

1.1: Ag₂O / dimethylformamide / 48 h / -30 °C

2.1: OsO₄; pyridine / diethyl ether / 12 h / 20 °C

2.2: 99.2 percent / NaHSO₃ / pyridine; H₂O / 12 h / 20 °C

3.1: 63.9 percent / p-TsOH*H₂O / 5 h / Heating

4.1: 90.9 percent / NaBH₄ / methanol / 3 h / -78 - 0 °C

5.1: 93.8 percent / NaH / dimethylformamide / 0.5 h / 0 °C

6.1: 84.7 percent / TBAF / tetrahydrofuran; hexane / 0.5 h / 0 °C

7.1: 71.5 percent / PCC; NaOAc; Celite / CH₂Cl₂ / 2 h / 20 °C

8.1: n-BuLi / tetrahydrofuran; hexane

8.2: 73.5 percent / tetrahydrofuran; hexane / -78 °C

9.1: NaBH₄ / ethanol; H₂O; tetrahydrofuran / 20 h / 4 °C

9.2: DMAP; pyridine / CH₂Cl₂ / 20 °C

9.3: Et₃N / CH₂Cl₂ / 20 °C

10.1: 86.1 percent / FeCl₃*SiO₂ / CHCl₃ / 2 h / 20 °C

With pyridine; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; Celite; tetrabutyl ammonium fluoride; sodium acetate; silica gel; iron(III) chloride; sodium hydride; toluene-4-sulfonic acid; pyridinium chlorochromate; silver(l) oxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; chloroform; water; N,N-dimethyl-formamide;
DOI:10.3987/COM-05-S(T)71