(2S,3S,4R,5R,6S,7S)-4-benzyloxy-1,2-O-isopropylidenedioxy-9-trimethylsilyl-8-nonyn-3,7-diol-5,6-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)]

Base Information

Chemical Name:(2S,3S,4R,5R,6S,7S)-4-benzyloxy-1,2-O-isopropylidenedioxy-9-trimethylsilyl-8-nonyn-3,7-diol-5,6-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)]
CAS No.:219967-31-4
Molecular Formula:C₃₀H₄₆O₉Si
Molecular Weight:578.775
Hs Code.:

Synonyms:(2S,3S,4R,5R,6S,7S)-4-benzyloxy-1,2-O-isopropylidenedioxy-9-trimethylsilyl-8-nonyn-3,7-diol-5,6-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)]

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S,3S,4R,5R,6S,7S)-4-benzyloxy-1,2-O-isopropylidenedioxy-9-trimethylsilyl-8-nonyn-3,7-diol-5,6-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)]

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Technology Process of (2S,3S,4R,5R,6S,7S)-4-benzyloxy-1,2-O-isopropylidenedioxy-9-trimethylsilyl-8-nonyn-3,7-diol-5,6-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)]

There total 14 articles about (2S,3S,4R,5R,6S,7S)-4-benzyloxy-1,2-O-isopropylidenedioxy-9-trimethylsilyl-8-nonyn-3,7-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: 85.0%

: 61210-52-4
(trimethylsilyl)ethynylmagnesium bromide

: 219967-30-3
(2S,3R,4R,5R,6R)-3-benzyloxy-6-hydroxy-2-[(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-3,4,5,6-tetrahydro-2H-pyran-4,5-bis[spiro-4''-(2'',2''-dimethyl-1'',3''-dioxolane)]

: 219967-31-4
(2S,3S,4R,5R,6S,7S)-4-benzyloxy-1,2-O-isopropylidenedioxy-9-trimethylsilyl-8-nonyn-3,7-diol-5,6-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)]

Guidance literature:: In tetrahydrofuran;
DOI:10.1055/s-1998-1988

Reference yield: 84.5%

: 219967-30-3
(2S,3R,4R,5R,6R)-3-benzyloxy-6-hydroxy-2-[(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-3,4,5,6-tetrahydro-2H-pyran-4,5-bis[spiro-4''-(2'',2''-dimethyl-1'',3''-dioxolane)]

: 1066-54-2
trimethylsilylacetylene

: 219967-31-4
(2S,3S,4R,5R,6S,7S)-4-benzyloxy-1,2-O-isopropylidenedioxy-9-trimethylsilyl-8-nonyn-3,7-diol-5,6-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)]

Guidance literature:: trimethylsilylacetylene; With ethylmagnesium chloride; In tetrahydrofuran;

(2S,3R,4R,5R,6R)-3-benzyloxy-6-hydroxy-2-[(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-3,4,5,6-tetrahydro-2H-pyran-4,5-bis[spiro-4''-(2'',2''-dimethyl-1'',3''-dioxolane)]; In tetrahydrofuran; at 20 ℃; for 40h;
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

: 219967-31-4
(2S,3S,4R,5R,6S,7S)-4-benzyloxy-1,2-O-isopropylidenedioxy-9-trimethylsilyl-8-nonyn-3,7-diol-5,6-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)]

Guidance literature:: Multi-step reaction with 7 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: EtMgCl / tetrahydrofuran

7.2: 84.5 percent / tetrahydrofuran / 40 h / 20 °C

With pyridine; sodium tetrahydroborate; osmium(VIII) oxide; tetrabutyl ammonium fluoride; ethylmagnesium chloride; sodium hydride; toluene-4-sulfonic acid; silver(l) oxide; In tetrahydrofuran; methanol; diethyl ether; hexane; N,N-dimethyl-formamide;
DOI:10.3987/COM-05-S(T)71