(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)]

Base Information

• Chemical Name: (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)]
• CAS No.: 882523-36-6
• Molecular Formula: C₃₀H₄₄O₉Si
• Molecular Weight: 576.759

Synonyms:(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)]

Chemical Property of (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)]

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Technology Process of (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)]

There total 14 articles about (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)] 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%

(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)] (219967-31-4) → (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)] (882523-36-6)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃;

DOI:10.3987/COM-05-S(T)71

Reference yield: 73.5%

(2S,3R,4R,5R)-3-benzyloxy-2-[(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-3,4,5,6-tetrahydro-2H-pyran-6-one-4,5-bis[spiro-4''-(2'',2''-dimethyl-1'',3''-dioxolane)] (882523-38-8) + trimethylsilylacetylene (1066-54-2) → (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)] (882523-36-6)

Guidance literature:

trimethylsilylacetylene; With n-butyllithium; In tetrahydrofuran; hexane;

(2S,3R,4R,5R)-3-benzyloxy-2-[(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-3,4,5,6-tetrahydro-2H-pyran-6-one-4,5-bis[spiro-4''-(2'',2''-dimethyl-1'',3''-dioxolane)]; In tetrahydrofuran; hexane; at -78 ℃;

DOI:10.3987/COM-05-S(T)71

Reference yield:

benzyl bromide (100-39-0) → (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)] (882523-36-6)

Guidance literature:

Multi-step reaction with 4 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

With n-butyllithium; Celite; tetrabutyl ammonium fluoride; sodium acetate; sodium hydride; pyridinium chlorochromate; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.3987/COM-05-S(T)71

upstream raw materials:

(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)]

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

trimethylsilylacetylene

benzyl bromide

Downstream raw materials:

(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)]

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

(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)]

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

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