(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)]

Base Information

Chemical Name:(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)]
CAS No.:219967-38-1
Molecular Formula:C₃₁H₅₀O₉Si
Molecular Weight:594.818
Hs Code.:

Synonyms:(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)]

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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 (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)]

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Technology Process of (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)]

There total 17 articles about (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)] 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: 100.0%

: 219967-37-0
(2R,3R,4R,5S,6S)-4-benzyloxy-5-tert-butyldimethylsiloxy-6,7-O-isopropylidenedioxy-1-heptanol-2,3-bis[spiro-4'-(2',2'-dimethyl-1',3'-dioxolane)]

: 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)]

Guidance literature:: With Dess-Martin periodane;
DOI:10.1055/s-1998-1988

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 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)]

Guidance literature:: Multi-step reaction with 3 steps

1: 92.7 percent / Et₃N / CH₂Cl₂ / 2 h / 20 °C

2: 91.3 percent / LiOH / methanol; H₂O / 1 h / 20 °C

3: 99.6 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

With lithium hydroxide; Dess-Martin periodane; triethylamine; In methanol; dichloromethane; water; 3: Dess-Martin oxidation;
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

: 219967-38-1
(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)]

Guidance literature:: Multi-step reaction with 11 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

9.1: 92.7 percent / Et₃N / CH₂Cl₂ / 2 h / 20 °C

10.1: 91.3 percent / LiOH / methanol; H₂O / 1 h / 20 °C

11.1: 99.6 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

With pyridine; dmap; lithium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; sodium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; silver(l) oxide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; 11.1: Dess-Martin oxidation;
DOI:10.3987/COM-05-S(T)71