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

Base Information

Chemical Name:(2S,3S,4R,5R,6S,7R)-1-acetoxy-4-benzyloxy-3-tert-butyldimethylsiloxy-7-methoxymethyloxy-8-nonyne-2-ol-5,6-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)]
CAS No.:219967-43-8
Molecular Formula:C₃₄H₅₄O₁₁Si
Molecular Weight:666.882
Hs Code.:

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

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

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

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

There total 21 articles about (2S,3S,4R,5R,6S,7R)-1-acetoxy-4-benzyloxy-3-tert-butyldimethylsiloxy-7-methoxymethyloxy-8-nonyne-2-ol-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: 97.0%

: 108-24-7
acetic anhydride

: 219967-42-7
(2S,3S,4R,5R,6S,7R)-4-benzyloxy-3-tert-butyldimethylsiloxy-7-methoxymethyloxy-8-nonyne-1,2-diol-5,6-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)]

: 219967-43-8
(2S,3S,4R,5R,6S,7R)-1-acetoxy-4-benzyloxy-3-tert-butyldimethylsiloxy-7-methoxymethyloxy-8-nonyne-2-ol-5,6-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)]

Guidance literature:: With pyridine; dmap; In dichloromethane;
DOI:10.1055/s-1998-1988

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 219967-43-8
(2S,3S,4R,5R,6S,7R)-1-acetoxy-4-benzyloxy-3-tert-butyldimethylsiloxy-7-methoxymethyloxy-8-nonyne-2-ol-5,6-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)]

Guidance literature:: Multi-step reaction with 8 steps

1.1: 92.7 percent / Et₃N / CH₂Cl₂ / 2 h / 20 °C

2.1: 91.3 percent / LiOH / methanol; H₂O / 1 h / 20 °C

3.1: 99.6 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

4.1: n-BuLi / tetrahydrofuran; hexane

4.2: 94.4 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C

5.1: 99.8 percent / K₂CO₃ / methanol / 2 h / 20 °C

6.1: 97.4 percent / i-Pr₂NEt / CH₂Cl₂ / 6 h / Heating

7.1: 68.1 percent / FeCl₃*SiO₂ / CHCl₃ / 20 °C

8.1: 96.7 percent / DMAP; pyridine / CH₂Cl₂ / 20 °C

With pyridine; dmap; lithium hydroxide; n-butyllithium; silica gel; iron(III) chloride; potassium carbonate; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; chloroform; water; 3.1: Dess-Martin oxidation;
DOI:10.3987/COM-05-S(T)71

Reference yield:

: 219967-25-6
(2S,4S,5R,6S)-6-tert-butyldimethylsiloxy-4,5-dihydroxy-4,5-bis(methoxymethyloxymethyl)-2-[(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-3,4,5,6-tetrahydro-2H-pyran-3-one

: 219967-43-8
(2S,3S,4R,5R,6S,7R)-1-acetoxy-4-benzyloxy-3-tert-butyldimethylsiloxy-7-methoxymethyloxy-8-nonyne-2-ol-5,6-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)]

Guidance literature:: Multi-step reaction with 14 steps

1.1: 63.9 percent / p-TsOH*H₂O / 5 h / Heating

2.1: 90.9 percent / NaBH₄ / methanol / 3 h / -78 - 0 °C

3.1: 93.8 percent / NaH / dimethylformamide / 0.5 h / 0 °C

4.1: 84.7 percent / TBAF / tetrahydrofuran; hexane / 0.5 h / 0 °C

5.1: 93.6 percent / LiAlH₄ / tetrahydrofuran / 1 h / 20 °C

6.1: 95.5 percent / DMAP; pyridine / CH₂Cl₂ / 1 h / 20 °C

7.1: 92.7 percent / Et₃N / CH₂Cl₂ / 2 h / 20 °C

8.1: 91.3 percent / LiOH / methanol; H₂O / 1 h / 20 °C

9.1: 99.6 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

10.1: n-BuLi / tetrahydrofuran; hexane

10.2: 94.4 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C

11.1: 99.8 percent / K₂CO₃ / methanol / 2 h / 20 °C

12.1: 97.4 percent / i-Pr₂NEt / CH₂Cl₂ / 6 h / Heating

13.1: 68.1 percent / FeCl₃*SiO₂ / CHCl₃ / 20 °C

14.1: 96.7 percent / DMAP; pyridine / CH₂Cl₂ / 20 °C

With pyridine; dmap; lithium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; tetrabutyl ammonium fluoride; silica gel; iron(III) chloride; sodium hydride; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; chloroform; water; N,N-dimethyl-formamide; 9.1: Dess-Martin oxidation;
DOI:10.3987/COM-05-S(T)71