(3Z)-5-bromo-6-O-tert-butyldiphenylsilyl-3,5-dideoxy-3-C-ethoxycarbonylmethylene-1,2-O-isopropylidene-β-L-lyxo-hex-3-enofuranose

Base Information

Chemical Name:(3Z)-5-bromo-6-O-tert-butyldiphenylsilyl-3,5-dideoxy-3-C-ethoxycarbonylmethylene-1,2-O-isopropylidene-β-L-lyxo-hex-3-enofuranose
CAS No.:188249-27-6
Molecular Formula:C₂₉H₃₇BrO₆Si
Molecular Weight:589.599
Hs Code.:

Synonyms:(3Z)-5-bromo-6-O-tert-butyldiphenylsilyl-3,5-dideoxy-3-C-ethoxycarbonylmethylene-1,2-O-isopropylidene-β-L-lyxo-hex-3-enofuranose

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Chemical Property of (3Z)-5-bromo-6-O-tert-butyldiphenylsilyl-3,5-dideoxy-3-C-ethoxycarbonylmethylene-1,2-O-isopropylidene-β-L-lyxo-hex-3-enofuranose

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Technology Process of (3Z)-5-bromo-6-O-tert-butyldiphenylsilyl-3,5-dideoxy-3-C-ethoxycarbonylmethylene-1,2-O-isopropylidene-β-L-lyxo-hex-3-enofuranose

There total 5 articles about (3Z)-5-bromo-6-O-tert-butyldiphenylsilyl-3,5-dideoxy-3-C-ethoxycarbonylmethylene-1,2-O-isopropylidene-β-L-lyxo-hex-3-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: 75.4%

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

: 188249-25-4
5-bromo-6-O-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-β-L-lyxo-hexos-3-ulofuranose

: 188249-27-6
(3Z)-5-bromo-6-O-tert-butyldiphenylsilyl-3,5-dideoxy-3-C-ethoxycarbonylmethylene-1,2-O-isopropylidene-β-L-lyxo-hex-3-enofuranose

Guidance literature:: In dichloromethane; at 0 - 20 ℃; for 7.67h;
DOI:10.1080/07328309708006509

Reference yield:

: 110920-92-8
(3aR,5R,6S,6aR)-5-((R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyethyl)-2,2-dimethyltetrahydrofuro(3,2-d)(1,3)dioxol-6-ol

: 188249-27-6
(3Z)-5-bromo-6-O-tert-butyldiphenylsilyl-3,5-dideoxy-3-C-ethoxycarbonylmethylene-1,2-O-isopropylidene-β-L-lyxo-hex-3-enofuranose

Guidance literature:: Multi-step reaction with 5 steps

1: ZnCl₂ / 6 h / 20 °C

2: N-bromosuccinimide; BaCO₃ / CCl₄ / 2.5 h / Heating

3: NaOMe; MeOH / 2.5 h / 20 °C

4: 81.2 percent / pyridinium dichromate; 3A molecular sieves; acetic acid / CH₂Cl₂ / 4.5 h / 20 °C

5: 75.4 percent / CH₂Cl₂ / 7.67 h / 0 - 20 °C

With methanol; N-Bromosuccinimide; dipyridinium dichromate; 3 A molecular sieve; sodium methylate; acetic acid; barium carbonate; zinc(II) chloride; In tetrachloromethane; dichloromethane; 1: acetalation / 2: Bromination / 3: debenzoylation / 4: Oxidation / 5: Wittig reaction;
DOI:10.1080/07328309708006509

Reference yield:

: 141242-26-4
3-O-benzoyl-5-bromo-6-O-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-β-L-idofuranose

: 188249-27-6
(3Z)-5-bromo-6-O-tert-butyldiphenylsilyl-3,5-dideoxy-3-C-ethoxycarbonylmethylene-1,2-O-isopropylidene-β-L-lyxo-hex-3-enofuranose

Guidance literature:: Multi-step reaction with 3 steps

1: NaOMe; MeOH / 2.5 h / 20 °C

2: 81.2 percent / pyridinium dichromate; 3A molecular sieves; acetic acid / CH₂Cl₂ / 4.5 h / 20 °C

3: 75.4 percent / CH₂Cl₂ / 7.67 h / 0 - 20 °C

With methanol; dipyridinium dichromate; 3 A molecular sieve; sodium methylate; acetic acid; In dichloromethane; 1: debenzoylation / 2: Oxidation / 3: Wittig reaction;
DOI:10.1080/07328309708006509