1,2-dideoxy-3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-5-O-tetrahydropyranyl-D-arabino-hex-1-ynitol

Base Information

• Chemical Name: 1,2-dideoxy-3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-5-O-tetrahydropyranyl-D-arabino-hex-1-ynitol
• CAS No.: 173033-02-8
• Molecular Formula: C₃₀H₄₀O₅Si
• Molecular Weight: 508.73

Synonyms:1,2-dideoxy-3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-5-O-tetrahydropyranyl-D-arabino-hex-1-ynitol

Chemical Property of 1,2-dideoxy-3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-5-O-tetrahydropyranyl-D-arabino-hex-1-ynitol

Chemical Property:

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Technology Process of 1,2-dideoxy-3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-5-O-tetrahydropyranyl-D-arabino-hex-1-ynitol

There total 5 articles about 1,2-dideoxy-3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-5-O-tetrahydropyranyl-D-arabino-hex-1-ynitol 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%

3,4-dihydro-2H-pyran (110-87-2) + 1,2-dideoxy-3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-D-arabino-hex-1-ynitol (173033-01-7) → 1,2-dideoxy-3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-5-O-tetrahydropyranyl-D-arabino-hex-1-ynitol (173033-02-8)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; at 0 - 20 ℃; for 25h;

DOI:10.1002/jlcr.2580361111

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → 1,2-dideoxy-3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-5-O-tetrahydropyranyl-D-arabino-hex-1-ynitol (173033-02-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / imidazole / dimethylformamide / 6 h / Ambient temperature

2: 96 percent / p-TsOH / CH₂Cl₂ / 25 h / 0 - 20 °C

With 1H-imidazole; toluene-4-sulfonic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/jlcr.2580361111

Reference yield:

(R)-1'-((4R,5R)-5-ethynyl-2,2-dimethyl-1,3-dioxolan-4-yl)ethane-1',2'-diol (173033-00-6) → 1,2-dideoxy-3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-5-O-tetrahydropyranyl-D-arabino-hex-1-ynitol (173033-02-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / imidazole / dimethylformamide / 6 h / Ambient temperature

2: 96 percent / p-TsOH / CH₂Cl₂ / 25 h / 0 - 20 °C

With 1H-imidazole; toluene-4-sulfonic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/jlcr.2580361111

upstream raw materials:

3,4-dihydro-2H-pyran

1,2-dideoxy-3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-D-arabino-hex-1-ynitol

tert-butylchlorodiphenylsilane

(R)-1'-((4R,5R)-5-ethynyl-2,2-dimethyl-1,3-dioxolan-4-yl)ethane-1',2'-diol

Downstream raw materials:

1,2-dideoxy-D-arabino-hex-1-enitol dibenzyl 6-phosphate

1,2-dideoxy-D-arabino-hex-1-ynitol dibenzyl 6-phosphate

1,2-dideoxy-3,4-O-isopropylidene-5-O-tetrahydropyranyl-D-arabino-hex-1-ynitol dibenzyl 6-phosphate

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