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

Base Information

Chemical Name:(2S,3R,4R,5S,6S)-1-acetoxy-4-benzyloxy-6,7-O-isopropylidenedioxy-5-heptanol-2,3-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)]
CAS No.:219967-35-8
Molecular Formula:C₂₇H₄₀O₁₀
Molecular Weight:524.609
Hs Code.:

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

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Chemical Property of (2S,3R,4R,5S,6S)-1-acetoxy-4-benzyloxy-6,7-O-isopropylidenedioxy-5-heptanol-2,3-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)]

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Technology Process of (2S,3R,4R,5S,6S)-1-acetoxy-4-benzyloxy-6,7-O-isopropylidenedioxy-5-heptanol-2,3-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)]

There total 14 articles about (2S,3R,4R,5S,6S)-1-acetoxy-4-benzyloxy-6,7-O-isopropylidenedioxy-5-heptanol-2,3-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: 96.0%

: 108-24-7
acetic anhydride

: 219967-34-7
(2R,3R,4R,5S,6S)-4-benzyloxy-6,7-O-isopropylidenedioxy-1,5-heptanediol-2,3-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)]

: 219967-35-8
(2S,3R,4R,5S,6S)-1-acetoxy-4-benzyloxy-6,7-O-isopropylidenedioxy-5-heptanol-2,3-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)]

Guidance literature:: With pyridine; In dichloromethane;
DOI:10.1055/s-1998-1988

Reference yield:

: 219967-25-6
(2S,4S,5R,6S)-6-tert-butyldimethylsiloxy-4,5-dihydroxy-4,5-bis(methoxymethyloxymethyl)-2-[(4'S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl]-3,4,5,6-tetrahydro-2H-pyran-3-one

: 219967-35-8
(2S,3R,4R,5S,6S)-1-acetoxy-4-benzyloxy-6,7-O-isopropylidenedioxy-5-heptanol-2,3-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)]

Guidance literature:: Multi-step reaction with 6 steps

1: 63.9 percent / p-TsOH*H₂O / 5 h / Heating

2: 90.9 percent / NaBH₄ / methanol / 3 h / -78 - 0 °C

3: 93.8 percent / NaH / dimethylformamide / 0.5 h / 0 °C

4: 84.7 percent / TBAF / tetrahydrofuran; hexane / 0.5 h / 0 °C

5: 93.6 percent / LiAlH₄ / tetrahydrofuran / 1 h / 20 °C

6: 95.5 percent / DMAP; pyridine / CH₂Cl₂ / 1 h / 20 °C

With pyridine; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;
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

: 219967-35-8
(2S,3R,4R,5S,6S)-1-acetoxy-4-benzyloxy-6,7-O-isopropylidenedioxy-5-heptanol-2,3-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)]

Guidance literature:: Multi-step reaction with 8 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: 93.6 percent / LiAlH₄ / tetrahydrofuran / 1 h / 20 °C

8.1: 95.5 percent / DMAP; pyridine / CH₂Cl₂ / 1 h / 20 °C

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