(1S,3R,4R,6S)-3-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>-4-<(4'-bromobenzyl)oxy>-2,7-dioxabicyclo<4.3.0>nonan-8-one

Base Information

Chemical Name:(1S,3R,4R,6S)-3-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>-4-<(4'-bromobenzyl)oxy>-2,7-dioxabicyclo<4.3.0>nonan-8-one
CAS No.:124581-47-1
Molecular Formula:C₂₁H₃₁BrO₅Si
Molecular Weight:471.464
Hs Code.:

Synonyms:(1S,3R,4R,6S)-3-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>-4-<(4'-bromobenzyl)oxy>-2,7-dioxabicyclo<4.3.0>nonan-8-one

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Chemical Property of (1S,3R,4R,6S)-3-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>-4-<(4'-bromobenzyl)oxy>-2,7-dioxabicyclo<4.3.0>nonan-8-one

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Technology Process of (1S,3R,4R,6S)-3-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>-4-<(4'-bromobenzyl)oxy>-2,7-dioxabicyclo<4.3.0>nonan-8-one

There total 12 articles about (1S,3R,4R,6S)-3-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>-4-<(4'-bromobenzyl)oxy>-2,7-dioxabicyclo<4.3.0>nonan-8-one 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: 90.0%

: 124581-45-9
(1S,3R,4S,5R,6R)-3-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>-4-<(4'-bromobenzyl)oxy>-5-(phenylseleno)-2,7-dioxabicyclo<4.3.0>nonan-8-one

: 124581-47-1
(1S,3R,4R,6S)-3-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>-4-<(4'-bromobenzyl)oxy>-2,7-dioxabicyclo<4.3.0>nonan-8-one

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 110 ℃; for 1.5h;
DOI:10.1021/jo00290a014

Reference yield:

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

: 124581-47-1
(1S,3R,4R,6S)-3-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>-4-<(4'-bromobenzyl)oxy>-2,7-dioxabicyclo<4.3.0>nonan-8-one

Guidance literature:: Multi-step reaction with 10 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

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

Reference yield:

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

: 124581-47-1
(1S,3R,4R,6S)-3-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>-4-<(4'-bromobenzyl)oxy>-2,7-dioxabicyclo<4.3.0>nonan-8-one

Guidance literature:: Multi-step reaction with 6 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

With sodium hydroxide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; potassium hydride; In methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; toluene; xylene;
DOI:10.1021/jo00290a014