(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)]

Base Information

• Chemical Name: (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)]
• CAS No.: 219967-30-3
• Molecular Formula: C₂₅H₃₆O₉
• Molecular Weight: 480.555
• Mol file: 219967-30-3.mol

Synonyms:(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)]

Chemical Property of (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)]

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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)]

There total 12 articles about (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)] 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: 95.0%

(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) → (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)] (219967-30-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1055/s-1998-1988

Reference yield:

(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 (219967-25-6) → (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)] (219967-30-3)

Guidance literature:

Multi-step reaction with 4 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

With sodium tetrahydroborate; tetrabutyl ammonium fluoride; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; hexane; 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,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)] (219967-30-3)

Guidance literature:

Multi-step reaction with 6 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

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

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

upstream raw materials:

(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)]

benzyl bromide

3,4-bis(methoxymethyloxymethyl)furan

(4S)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

Downstream 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)]

(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)]

(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)]