(5S)-3-O-Benzyl-6,7-dideoxy-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribo-hept-6-enofuranose

Base Information

Chemical Name:(5S)-3-O-Benzyl-6,7-dideoxy-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribo-hept-6-enofuranose
CAS No.:352422-85-6
Molecular Formula:C₁₉H₂₄O₅
Molecular Weight:332.397
Hs Code.:

Synonyms:(5S)-3-O-Benzyl-6,7-dideoxy-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribo-hept-6-enofuranose

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Chemical Property of (5S)-3-O-Benzyl-6,7-dideoxy-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribo-hept-6-enofuranose

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Technology Process of (5S)-3-O-Benzyl-6,7-dideoxy-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribo-hept-6-enofuranose

There total 4 articles about (5S)-3-O-Benzyl-6,7-dideoxy-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribo-hept-6-enofuranose 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:

: 96212-44-1
(3aR,5R,6R,6aR)-6-(benzyloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-vinyltetrahydrofuro-[2,3-d][1,3]dioxole

: 352422-85-6
(5S)-3-O-Benzyl-6,7-dideoxy-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribo-hept-6-enofuranose

Guidance literature:: Multi-step reaction with 2 steps

1: periodic acid / ethyl acetate / 1 h / 20 °C

2: tetrahydrofuran / 48 h / 20 °C

With periodic acid; In tetrahydrofuran; ethyl acetate; 2: Grignard addition;
DOI:10.1039/b101364p

Reference yield:

: 51996-47-5
(3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-vinyltetrahydrofuro[2,3-d][1,3]-dioxol-6-ol

: 352422-85-6
(5S)-3-O-Benzyl-6,7-dideoxy-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribo-hept-6-enofuranose

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 50 °C

1.2: 27 / 16 h / 20 °C

2.1: periodic acid / ethyl acetate / 1 h / 20 °C

3.1: tetrahydrofuran / 48 h / 20 °C

With sodium hydride; periodic acid; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide; 3.1: Grignard addition;
DOI:10.1039/b101364p

Reference yield:

: 100-39-0
benzyl bromide

: 352422-85-6
(5S)-3-O-Benzyl-6,7-dideoxy-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribo-hept-6-enofuranose

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 50 °C

1.2: 27 / 16 h / 20 °C

2.1: periodic acid / ethyl acetate / 1 h / 20 °C

3.1: tetrahydrofuran / 48 h / 20 °C

With sodium hydride; periodic acid; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide; 3.1: Grignard addition;
DOI:10.1039/b101364p