(6R)-3-benzyloxyimino-1,2:5,6-di-O-isopropylidene-6-(prop-2-ynyl)-α-D-ribohexofuranose

Base Information

Chemical Name:(6R)-3-benzyloxyimino-1,2:5,6-di-O-isopropylidene-6-(prop-2-ynyl)-α-D-ribohexofuranose
CAS No.:911407-82-4
Molecular Formula:C₂₂H₂₇NO₆
Molecular Weight:401.459
Hs Code.:

Synonyms:(6R)-3-benzyloxyimino-1,2:5,6-di-O-isopropylidene-6-(prop-2-ynyl)-α-D-ribohexofuranose

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Chemical Property of (6R)-3-benzyloxyimino-1,2:5,6-di-O-isopropylidene-6-(prop-2-ynyl)-α-D-ribohexofuranose

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Technology Process of (6R)-3-benzyloxyimino-1,2:5,6-di-O-isopropylidene-6-(prop-2-ynyl)-α-D-ribohexofuranose

There total 8 articles about (6R)-3-benzyloxyimino-1,2:5,6-di-O-isopropylidene-6-(prop-2-ynyl)-α-D-ribohexofuranose 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%

: 911407-81-3
(6R)-3-benzyloxyimino-1,2:5,6-di-O-isopropylidene-6-(3-trimethylsilyl-prop-2-ynyl)-α-D-ribohexofuranose

: 911407-82-4
(6R)-3-benzyloxyimino-1,2:5,6-di-O-isopropylidene-6-(prop-2-ynyl)-α-D-ribohexofuranose

Guidance literature:: With potassium carbonate; In methanol; at 20 ℃; for 7h;
DOI:10.1021/jo060883y

Reference yield:

: 1,2-O-isopropylidene-6-(3-trimethylsilyl-prop-2-ynyl)-α-D-glucofuranose

: 911407-82-4
(6R)-3-benzyloxyimino-1,2:5,6-di-O-isopropylidene-6-(prop-2-ynyl)-α-D-ribohexofuranose

Guidance literature:: Multi-step reaction with 3 steps

1.1: p-TsOH / acetone / Heating

2.1: Dess-Martin periodinane / 2-methyl-propan-2-ol; acetonitrile / 20 °C

2.2: 830 mg / KOAc / toluene / 4 h / Heating

3.1: 97 percent / K₂CO₃ / methanol / 7 h / 20 °C

With potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; In methanol; acetone; acetonitrile; tert-butyl alcohol; 2.1: Dess-Martin oxidation;
DOI:10.1021/jo060883y

Reference yield:

: 911407-77-7
1,2-O-isopropylidene-5-O-methoxymethyl-glucurono-γ-lactone

: 911407-82-4
(6R)-3-benzyloxyimino-1,2:5,6-di-O-isopropylidene-6-(prop-2-ynyl)-α-D-ribohexofuranose

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-BuLi / hexane; tetrahydrofuran / 1 h / -78 °C

1.2: 75 percent / tetrahydrofuran; hexane / 0 °C

2.1: 88 percent / NaBH₄ / methanol / 0 °C

3.1: 32 percent / p-TsOH / acetone / 20 °C

4.1: Dess-Martin periodinane / 2-methyl-propan-2-ol; acetonitrile / 20 °C

4.2: 830 mg / KOAc / toluene / 4 h / Heating

5.1: 97 percent / K₂CO₃ / methanol / 7 h / 20 °C

With sodium tetrahydroborate; n-butyllithium; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; hexane; acetone; acetonitrile; tert-butyl alcohol; 4.1: Dess-Martin oxidation;
DOI:10.1021/jo060883y