(2R,3S,5S,6R)-5-benzyloxy-6-benzyloxymethyl-2-prop-2-ynyl-3-acetoxytetrahydropyran

Base Information

Chemical Name:(2R,3S,5S,6R)-5-benzyloxy-6-benzyloxymethyl-2-prop-2-ynyl-3-acetoxytetrahydropyran
CAS No.:796128-16-0
Molecular Formula:C₂₅H₂₈O₅
Molecular Weight:408.494
Hs Code.:

Synonyms:(2R,3S,5S,6R)-5-benzyloxy-6-benzyloxymethyl-2-prop-2-ynyl-3-acetoxytetrahydropyran

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Chemical Property of (2R,3S,5S,6R)-5-benzyloxy-6-benzyloxymethyl-2-prop-2-ynyl-3-acetoxytetrahydropyran

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Technology Process of (2R,3S,5S,6R)-5-benzyloxy-6-benzyloxymethyl-2-prop-2-ynyl-3-acetoxytetrahydropyran

There total 4 articles about (2R,3S,5S,6R)-5-benzyloxy-6-benzyloxymethyl-2-prop-2-ynyl-3-acetoxytetrahydropyran 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:

: 796128-04-6
(2R,3S)-3-(benzyloxy)hex-5-yne-1,2-diol

: 796128-16-0
(2R,3S,5S,6R)-5-benzyloxy-6-benzyloxymethyl-2-prop-2-ynyl-3-acetoxytetrahydropyran

Guidance literature:: Multi-step reaction with 4 steps

1.1: 70 percent / CpRu[P(p-F-C₆H₄)3]2Cl; P(p-FC₆H₄)3; N-hydroxysuccinimide sodium salt / tetra-n-butylammonium hexafluorophosphate / dimethylformamide / 26 h / 85 °C

2.1: NaH / dimethylformamide / 0.5 h / 0 °C

2.2: 77 percent / dimethylformamide / 4 h / 0 °C

3.1: dimethyldioxirane / CH₂Cl₂; acetone / 0.5 h / -78 °C

4.1: diethyl ether / 2 h / -78 °C

4.2: 25 mg / Et₃N / CH₂Cl₂ / 1 h / 0 °C

With (η(5)-C5H5)RuCl(P(p-FC6H4)3)2; 3,3-dimethyldioxirane; sodium hydride; sodium salt of N-hydroxysuccinimide; P(p-C₆H₄F)3; tert-butylammonium hexafluorophosphate(V); In diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1021/ol048165q

Reference yield:

: 108-24-7
acetic anhydride

: 18295-60-8
allenylmagnesium bromide

: (3R,4S)-4-Benzyloxy-3-benzyloxymethyl-2,7-dioxa-bicyclo[4.1.0]heptane

: 796128-15-9
(2S,3R,5S,6R)-5-benzyloxy-6-benzyloxymethyl-2-prop-2-ynyl-3-acetoxytetrahydropyran

: 796128-16-0
(2R,3S,5S,6R)-5-benzyloxy-6-benzyloxymethyl-2-prop-2-ynyl-3-acetoxytetrahydropyran

Guidance literature:: allenylmagnesium bromide; (3R,4S)-4-Benzyloxy-3-benzyloxymethyl-2,7-dioxa-bicyclo[4.1.0]heptane; In diethyl ether; at -78 ℃; for 2h;

acetic anhydride; With triethylamine; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1021/ol048165q

Reference yield:

: 117399-55-0
1,5-anhydro-4,6-di-O-benzyl-D-erythro-hex-1-enitol

: 796128-16-0
(2R,3S,5S,6R)-5-benzyloxy-6-benzyloxymethyl-2-prop-2-ynyl-3-acetoxytetrahydropyran

Guidance literature:: Multi-step reaction with 2 steps

1.1: dimethyldioxirane / CH₂Cl₂; acetone / 0.5 h / -78 °C

2.1: diethyl ether / 2 h / -78 °C

2.2: 25 mg / Et₃N / CH₂Cl₂ / 1 h / 0 °C

With 3,3-dimethyldioxirane; In diethyl ether; dichloromethane; acetone;
DOI:10.1021/ol048165q