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

Base Information

Chemical Name:(2S,3S,4R,5R,6S,7R)-4-benzyloxy-3-tert-butyldimethylsiloxy-1,2-O-isopropylidenedioxy-9-trimethylsilyl-8-nonyn-7-ol-5,6-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)]
CAS No.:219967-39-2
Molecular Formula:C₃₆H₆₀O₉Si₂
Molecular Weight:693.038
Hs Code.:

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

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

There total 19 articles about (2S,3S,4R,5R,6S,7R)-4-benzyloxy-3-tert-butyldimethylsiloxy-1,2-O-isopropylidenedioxy-9-trimethylsilyl-8-nonyn-7-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: 94.4%

: 219967-38-1
(2R,3R,4R,5S,6S)-4-benzyloxy-5-tert-butyldimethylsiloxy-6,7-O-isopropylidenedioxypentanal-2,3-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)]

: 1066-54-2
trimethylsilylacetylene

: 219967-39-2
(2S,3S,4R,5R,6S,7R)-4-benzyloxy-3-tert-butyldimethylsiloxy-1,2-O-isopropylidenedioxy-9-trimethylsilyl-8-nonyn-7-ol-5,6-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)]

Guidance literature:: trimethylsilylacetylene; With n-butyllithium; In tetrahydrofuran; hexane;

(2R,3R,4R,5S,6S)-4-benzyloxy-5-tert-butyldimethylsiloxy-6,7-O-isopropylidenedioxypentanal-2,3-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)]; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;
DOI:10.3987/COM-05-S(T)71

Reference yield: 94.0%

: 54655-07-1
lithium trimethylsilylacetylenide

: 219967-38-1
(2R,3R,4R,5S,6S)-4-benzyloxy-5-tert-butyldimethylsiloxy-6,7-O-isopropylidenedioxypentanal-2,3-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)]

: 219967-39-2
(2S,3S,4R,5R,6S,7R)-4-benzyloxy-3-tert-butyldimethylsiloxy-1,2-O-isopropylidenedioxy-9-trimethylsilyl-8-nonyn-7-ol-5,6-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)]

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

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 219967-39-2
(2S,3S,4R,5R,6S,7R)-4-benzyloxy-3-tert-butyldimethylsiloxy-1,2-O-isopropylidenedioxy-9-trimethylsilyl-8-nonyn-7-ol-5,6-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)]

Guidance literature:: Multi-step reaction with 4 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

With lithium hydroxide; n-butyllithium; Dess-Martin periodane; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; water; 3.1: Dess-Martin oxidation;
DOI:10.3987/COM-05-S(T)71