(2S,3S,4R,5R,6S,7S)-4-benzyloxy-1,2-O-isopropylidenedioxy-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-8-nonyn-3,7-diol-5,6-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)]
CAS No.:882523-33-3
Molecular Formula:C₂₇H₃₈O₉
Molecular Weight:506.593
Hs Code.:

Synonyms:(2S,3S,4R,5R,6S,7S)-4-benzyloxy-1,2-O-isopropylidenedioxy-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-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-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-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: 65.3%

: 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)]

: 882523-33-3
(2S,3S,4R,5R,6S,7S)-4-benzyloxy-1,2-O-isopropylidenedioxy-8-nonyn-3,7-diol-5,6-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)]

Guidance literature:: With potassium carbonate; In methanol; at 20 ℃;
DOI:10.3987/COM-05-S(T)71

Reference yield:

: 882523-36-6
(2S,3R,4R,5R)-3-benzyloxy-6-hydroxy-2-[(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-6-trimethylsilylethynyl-3,4,5,6-tetrahydro-2H-pyran-4,5-bis[spiro-4''-(2'',2''-dimethyl-1'',3''-dioxolane)]

: 882523-33-3
(2S,3S,4R,5R,6S,7S)-4-benzyloxy-1,2-O-isopropylidenedioxy-8-nonyn-3,7-diol-5,6-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)]

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

Guidance literature:: With sodium tetrahydroborate; In tetrahydrofuran; ethanol; water; at 4 ℃; for 20h; Title compound not separated from byproducts;
DOI:10.3987/COM-05-S(T)71

Reference yield:

: 100-39-0
benzyl bromide

: 882523-33-3
(2S,3S,4R,5R,6S,7S)-4-benzyloxy-1,2-O-isopropylidenedioxy-8-nonyn-3,7-diol-5,6-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)]

Guidance literature:: Multi-step reaction with 5 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

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