(2S,3R,4R,5R,6S)-3-benzyloxy-6-tert-butyldimethylsiloxy-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)]

Base Information

• Chemical Name: (2S,3R,4R,5R,6S)-3-benzyloxy-6-tert-butyldimethylsiloxy-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)]
• CAS No.: 219967-29-0
• Molecular Formula: C₃₁H₅₀O₉Si
• Molecular Weight: 594.818

Synonyms:(2S,3R,4R,5R,6S)-3-benzyloxy-6-tert-butyldimethylsiloxy-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)]

Chemical Property of (2S,3R,4R,5R,6S)-3-benzyloxy-6-tert-butyldimethylsiloxy-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)]

Chemical Property:

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Technology Process of (2S,3R,4R,5R,6S)-3-benzyloxy-6-tert-butyldimethylsiloxy-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)]

There total 10 articles about (2S,3R,4R,5R,6S)-3-benzyloxy-6-tert-butyldimethylsiloxy-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)] 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: 94.0%

benzyl bromide (100-39-0) + (2S,3R,4R,5R,6S)-6-tert-butyldimethylsiloxy-3-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)] (219967-27-8) → (2S,3R,4R,5R,6S)-3-benzyloxy-6-tert-butyldimethylsiloxy-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)] (219967-29-0)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1055/s-1998-1988

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (2S,3R,4R,5R,6S)-3-benzyloxy-6-tert-butyldimethylsiloxy-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)] (219967-29-0)

Guidance literature:

Multi-step reaction with 5 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

With pyridine; sodium tetrahydroborate; osmium(VIII) oxide; sodium hydride; toluene-4-sulfonic acid; silver(l) oxide; In methanol; diethyl ether; N,N-dimethyl-formamide;

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

Reference yield:

(2S)-6-hydroxy-2-[(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-4,5-bis(methoxymethyloxymethyl)-6H-pyran-3(2H)-one (882523-27-5) → (2S,3R,4R,5R,6S)-3-benzyloxy-6-tert-butyldimethylsiloxy-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)] (219967-29-0)

Guidance literature:

Multi-step reaction with 5 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

With pyridine; sodium tetrahydroborate; osmium(VIII) oxide; sodium hydride; toluene-4-sulfonic acid; silver(l) oxide; In methanol; diethyl ether; N,N-dimethyl-formamide;

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

upstream raw materials:

benzyl bromide

(2S,3R,4R,5R,6S)-6-tert-butyldimethylsiloxy-3-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)]

tert-butyldimethylsilyl chloride

3,4-bis(methoxymethyloxymethyl)furan

Downstream raw materials:

(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)]

(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)]

(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,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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