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

Base Information

Chemical Name: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
CAS No.:1453217-90-7
Molecular Formula:C₄₅H₆₀O₆Si₂
Molecular Weight:753.139
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 8 articles about 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 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: 98.0%

: 69739-34-0
t-butyldimethylsiyl triflate

(S)-1-((3aR,5S,6S,6aR)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-6-(naphthalen-2-ylmethoxy)tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)but-3-en-1-ol: 1453217-78-1
(S)-1-((3aR,5S,6S,6aR)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-6-(naphthalen-2-ylmethoxy)tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)but-3-en-1-ol

: 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

Guidance literature:: With pyridine; In dichloromethane; at 0 - 23 ℃; for 3h; 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

: 1453217-90-7
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

Guidance literature:: Multi-step reaction with 3 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

With pyridine; boron trifluoride diethyl etherate; pyridinium chlorochromate; In dichloromethane; 2.1: |Sakurai Allylation;
DOI:10.1021/jo401170y

Reference yield:

(3aR,5R,6S,6aR)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-6-(naphthalen-2-ylmethoxy)tetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde: (3aR,5R,6S,6aR)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-6-(naphthalen-2-ylmethoxy)tetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde

: 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

Guidance literature:: Multi-step reaction with 2 steps

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

1.2: 2 h / -41 °C / Inert atmosphere

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

With pyridine; boron trifluoride diethyl etherate; In dichloromethane; 1.1: |Sakurai Allylation;
DOI:10.1021/jo401170y