1,2-O-isopropylidene-3-keto-4-C-(tert-butyldiphenylsilyl)oxymethyl-5-O-(tert-butyldimethylsilyl)-6-deoxy-6-C-vinyl-β-Lmannofuranose

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Chemical Name:1,2-O-isopropylidene-3-keto-4-C-(tert-butyldiphenylsilyl)oxymethyl-5-O-(tert-butyldimethylsilyl)-6-deoxy-6-C-vinyl-β-Lmannofuranose
CAS No.:1453217-91-8
Molecular Formula:C₃₄H₅₀O₆Si₂
Molecular Weight:610.938
Hs Code.:

Synonyms:1,2-O-isopropylidene-3-keto-4-C-(tert-butyldiphenylsilyl)oxymethyl-5-O-(tert-butyldimethylsilyl)-6-deoxy-6-C-vinyl-β-Lmannofuranose

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Chemical Property of 1,2-O-isopropylidene-3-keto-4-C-(tert-butyldiphenylsilyl)oxymethyl-5-O-(tert-butyldimethylsilyl)-6-deoxy-6-C-vinyl-β-Lmannofuranose

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Technology Process of 1,2-O-isopropylidene-3-keto-4-C-(tert-butyldiphenylsilyl)oxymethyl-5-O-(tert-butyldimethylsilyl)-6-deoxy-6-C-vinyl-β-Lmannofuranose

There total 9 articles about 1,2-O-isopropylidene-3-keto-4-C-(tert-butyldiphenylsilyl)oxymethyl-5-O-(tert-butyldimethylsilyl)-6-deoxy-6-C-vinyl-β-Lmannofuranose 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: 97.0%

: 1453217-92-9
C₃₄H₅₂O₆Si₂

: 1453217-91-8
1,2-O-isopropylidene-3-keto-4-C-(tert-butyldiphenylsilyl)oxymethyl-5-O-(tert-butyldimethylsilyl)-6-deoxy-6-C-vinyl-β-Lmannofuranose

Guidance literature:: With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 23 ℃; for 18h; Inert atmosphere;
DOI:10.1021/jo401170y

Reference yield:

: 956485-08-8
((3aR,5R,6S,6aR)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-6-(naphthalen-2-ylmethoxy)tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol

: 1453217-91-8
1,2-O-isopropylidene-3-keto-4-C-(tert-butyldiphenylsilyl)oxymethyl-5-O-(tert-butyldimethylsilyl)-6-deoxy-6-C-vinyl-β-Lmannofuranose

Guidance literature:: Multi-step reaction with 5 steps

1.1: pyridinium chlorochromate / dichloromethane / 13 h / 40 °C / Inert atmosphere

2.1: boron trifluoride diethyl etherate / dichloromethane / 0.08 h / -41 °C / Inert atmosphere

2.2: 2 h / -41 °C / Inert atmosphere

3.1: pyridine / dichloromethane / 3 h / 0 - 23 °C / Inert atmosphere

4.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 6 h / 23 °C

5.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 18 h / 23 °C / Inert atmosphere

With pyridine; boron trifluoride diethyl etherate; sodium hydrogencarbonate; Dess-Martin periodane; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; 2.1: |Sakurai Allylation / 5.1: |Wacker Oxidation;
DOI:10.1021/jo401170y

Reference yield:

: 1453217-90-7
1,2-O-isopropylidene-3-O-(2-naphthylmethyl)-4-C-(tert-butyldiphenylsilyl)oxymethyl-5-O-(tert-butyldimethylsilyl)-6-deoxy-6-C-vinyl-β-L-mannofuranose

: 1453217-91-8
1,2-O-isopropylidene-3-keto-4-C-(tert-butyldiphenylsilyl)oxymethyl-5-O-(tert-butyldimethylsilyl)-6-deoxy-6-C-vinyl-β-Lmannofuranose

Guidance literature:: Multi-step reaction with 2 steps

1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 6 h / 23 °C

2: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 18 h / 23 °C / Inert atmosphere

With sodium hydrogencarbonate; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; 2: |Wacker Oxidation;
DOI:10.1021/jo401170y