4-[(2R,3S,4R,5S)-3-Benzyloxy-2,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-6-nitro-hexylidene]-2,6-dimethoxy-cyclohexa-2,5-dienone

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Chemical Name:4-[(2R,3S,4R,5S)-3-Benzyloxy-2,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-6-nitro-hexylidene]-2,6-dimethoxy-cyclohexa-2,5-dienone
CAS No.:199851-15-5
Molecular Formula:C₃₉H₆₇NO₉Si₃
Molecular Weight:778.219
Hs Code.:

Synonyms:4-[(2R,3S,4R,5S)-3-Benzyloxy-2,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-6-nitro-hexylidene]-2,6-dimethoxy-cyclohexa-2,5-dienone

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Chemical Property of 4-[(2R,3S,4R,5S)-3-Benzyloxy-2,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-6-nitro-hexylidene]-2,6-dimethoxy-cyclohexa-2,5-dienone

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Technology Process of 4-[(2R,3S,4R,5S)-3-Benzyloxy-2,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-6-nitro-hexylidene]-2,6-dimethoxy-cyclohexa-2,5-dienone

There total 11 articles about 4-[(2R,3S,4R,5S)-3-Benzyloxy-2,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-6-nitro-hexylidene]-2,6-dimethoxy-cyclohexa-2,5-dienone 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: 96.0%

: 199851-14-4
4-[(2R,3S,4R,5S)-3-Benzyloxy-2,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-6-nitro-hexyl]-2,6-dimethoxy-phenol

: 199851-15-5
4-[(2R,3S,4R,5S)-3-Benzyloxy-2,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-6-nitro-hexylidene]-2,6-dimethoxy-cyclohexa-2,5-dienone

Guidance literature:: With silver(l) oxide; In chloroform-d1; at 24 - 57 ℃; for 14h; ultrasound;
DOI:10.1016/S0040-4039(97)10138-1

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 199851-15-5
4-[(2R,3S,4R,5S)-3-Benzyloxy-2,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-6-nitro-hexylidene]-2,6-dimethoxy-cyclohexa-2,5-dienone

Guidance literature:: Multi-step reaction with 3 steps

1: 91 percent / 2,6-lutidine / CH₂Cl₂ / 44 h / 0 - 20 °C

2: 88 percent / camphorsulphonic acid / methanol / 4 h / Ambient temperature

3: 96 percent / silver(I) oxid / CDCl₃ / 14 h / 24 - 57 °C / ultrasound

With 2,6-dimethylpyridine; camphor-10-sulfonic acid; silver(l) oxide; In methanol; chloroform-d1; dichloromethane;
DOI:10.1016/S0040-4039(97)10138-1

Reference yield:

: 23558-05-6
3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose

: 199851-15-5
4-[(2R,3S,4R,5S)-3-Benzyloxy-2,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-6-nitro-hexylidene]-2,6-dimethoxy-cyclohexa-2,5-dienone

Guidance literature:: Multi-step reaction with 10 steps

1: 85 percent / tetrahydrofuran / -78 - 0 °C

2: 1.) MsCl, Et₃N, 2.) LiAlH₄ / 1.) ether, 0 deg C, 30 min, 2.) ether, 0 deg C to r.t., 20 min

3: 86 percent / MgBr₂*OEt₂ / diethyl ether / 21 h / 0 - 20 °C

4: 100 percent / CSA / benzene / 0.33 h / Ambient temperature

5: 87 percent / HgCl₂, HgO / acetonitrile; H₂O / 0.33 h / Ambient temperature

6: 83 percent / t-BuOK / tetrahydrofuran / 0.58 h / 0 °C

7: 82 percent / ethanethiol, SnCl₂ / CH₂Cl₂ / 20 h / Ambient temperature

8: 91 percent / 2,6-lutidine / CH₂Cl₂ / 44 h / 0 - 20 °C

9: 88 percent / camphorsulphonic acid / methanol / 4 h / Ambient temperature

10: 96 percent / silver(I) oxid / CDCl₃ / 14 h / 24 - 57 °C / ultrasound

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; camphor-10-sulfonic acid; potassium tert-butylate; methanesulfonyl chloride; triethylamine; ethanethiol; mercury dichloride; tin(ll) chloride; mercury(II) oxide; magnesium bromide; silver(l) oxide; In tetrahydrofuran; methanol; diethyl ether; chloroform-d1; dichloromethane; water; acetonitrile; benzene;
DOI:10.1016/S0040-4039(97)10138-1