(1S,3R,4R,6S,8R)-4-<(4'-bromobenzyl)oxy>-8-(methyloxy)-3-(2-oxoethyl)-2,7-dioxabicyclo<4.3.0>nonane

Base Information

Chemical Name:(1S,3R,4R,6S,8R)-4-<(4'-bromobenzyl)oxy>-8-(methyloxy)-3-(2-oxoethyl)-2,7-dioxabicyclo<4.3.0>nonane
CAS No.:124581-52-8
Molecular Formula:C₁₇H₂₁BrO₅
Molecular Weight:385.255
Hs Code.:

Synonyms:(1S,3R,4R,6S,8R)-4-<(4'-bromobenzyl)oxy>-8-(methyloxy)-3-(2-oxoethyl)-2,7-dioxabicyclo<4.3.0>nonane

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Chemical Property of (1S,3R,4R,6S,8R)-4-<(4'-bromobenzyl)oxy>-8-(methyloxy)-3-(2-oxoethyl)-2,7-dioxabicyclo<4.3.0>nonane

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Technology Process of (1S,3R,4R,6S,8R)-4-<(4'-bromobenzyl)oxy>-8-(methyloxy)-3-(2-oxoethyl)-2,7-dioxabicyclo<4.3.0>nonane

There total 16 articles about (1S,3R,4R,6S,8R)-4-<(4'-bromobenzyl)oxy>-8-(methyloxy)-3-(2-oxoethyl)-2,7-dioxabicyclo<4.3.0>nonane 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: 77.0%

: 124602-52-4
(1S,3R,4R,6S,8R)-4-<(4'-bromobenzyl)oxy>-3-(cyanomethyl)-8-(methyloxy)-2,7-dioxabicyclo<4.3.0>nonane

: 124581-52-8
(1S,3R,4R,6S,8R)-4-<(4'-bromobenzyl)oxy>-8-(methyloxy)-3-(2-oxoethyl)-2,7-dioxabicyclo<4.3.0>nonane

Guidance literature:: With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃; for 2h;
DOI:10.1021/jo00290a014

Reference yield:

: 3068-32-4
1-bromo-2,3,4,6-tetra-O-acetyl-D-galactopyranose

: 124581-52-8
(1S,3R,4R,6S,8R)-4-<(4'-bromobenzyl)oxy>-8-(methyloxy)-3-(2-oxoethyl)-2,7-dioxabicyclo<4.3.0>nonane

Guidance literature:: Multi-step reaction with 14 steps

1: zinc dust / aq. acetic acid / 1 h / 0 °C

2: NH₃ / methanol / 15 h / Ambient temperature

3: 73 percent / pyridine / 1) 0 deg C, 1 h, 2) RT, 15 h

4: 95 percent / pyridine / 1) - 35 deg C, 1.5 h, 2) up to 0 deg C, 30 min

5: KH / hexamethylphosphoric acid triamide / 1.5 h / 0 °C

6: 10percent aq. NaOH / methanol / 15 h / Ambient temperature

7: 95 percent / xylene / 10 h / 142 °C

8: 4.4 percent / CH₂Cl₂ / 2 h / -78 °C

10: 90 percent / n-Bu₃SnH, AIBN / toluene / 1.5 h / 110 °C

11: DIBAL / toluene; hexane / 2 h / -78 °C

12: p-TsOH / 2 h / Ambient temperature

13: 1) triflic anhydride, pyridine, 2) NaCN / CH₂Cl₂, 1) - 42 deg C, 5 min, 2) HMPA, RT, 7 h

14: 77 percent / DIBAL / CH₂Cl₂; hexane / 2 h / -78 °C

With pyridine; sodium hydroxide; 2,2'-azobis(isobutyronitrile); trifluoromethylsulfonic anhydride; sodium cyanide; ammonia; tri-n-butyl-tin hydride; potassium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; zinc; In methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; acetic acid; toluene; xylene;
DOI:10.1021/jo00290a014

Reference yield:

: 124648-31-3
6-((tert-butyldimethylsilyl)oxy)-3-O-benzoyl-D-galactal

: 124581-52-8
(1S,3R,4R,6S,8R)-4-<(4'-bromobenzyl)oxy>-8-(methyloxy)-3-(2-oxoethyl)-2,7-dioxabicyclo<4.3.0>nonane

Guidance literature:: Multi-step reaction with 10 steps

1: KH / hexamethylphosphoric acid triamide / 1.5 h / 0 °C

2: 10percent aq. NaOH / methanol / 15 h / Ambient temperature

3: 95 percent / xylene / 10 h / 142 °C

4: 4.4 percent / CH₂Cl₂ / 2 h / -78 °C

6: 90 percent / n-Bu₃SnH, AIBN / toluene / 1.5 h / 110 °C

7: DIBAL / toluene; hexane / 2 h / -78 °C

8: p-TsOH / 2 h / Ambient temperature

9: 1) triflic anhydride, pyridine, 2) NaCN / CH₂Cl₂, 1) - 42 deg C, 5 min, 2) HMPA, RT, 7 h

10: 77 percent / DIBAL / CH₂Cl₂; hexane / 2 h / -78 °C

With pyridine; sodium hydroxide; 2,2'-azobis(isobutyronitrile); trifluoromethylsulfonic anhydride; sodium cyanide; tri-n-butyl-tin hydride; potassium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; In methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; toluene; xylene;
DOI:10.1021/jo00290a014