(3S,4R,5R)-3,4-syn-6-(Benzyloxy)-5-((tert-butyldimethylsilyl)oxy)-4-(methoxymethoxy)hex-1-en-3-ol

Base Information

Chemical Name:(3S,4R,5R)-3,4-syn-6-(Benzyloxy)-5-((tert-butyldimethylsilyl)oxy)-4-(methoxymethoxy)hex-1-en-3-ol
CAS No.:156568-08-0
Molecular Formula:C₂₁H₃₆O₅Si
Molecular Weight:396.599
Hs Code.:

Synonyms:(3S,4R,5R)-3,4-syn-6-(Benzyloxy)-5-((tert-butyldimethylsilyl)oxy)-4-(methoxymethoxy)hex-1-en-3-ol

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Chemical Property of (3S,4R,5R)-3,4-syn-6-(Benzyloxy)-5-((tert-butyldimethylsilyl)oxy)-4-(methoxymethoxy)hex-1-en-3-ol

Chemical Property:

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Technology Process of (3S,4R,5R)-3,4-syn-6-(Benzyloxy)-5-((tert-butyldimethylsilyl)oxy)-4-(methoxymethoxy)hex-1-en-3-ol

There total 11 articles about (3S,4R,5R)-3,4-syn-6-(Benzyloxy)-5-((tert-butyldimethylsilyl)oxy)-4-(methoxymethoxy)hex-1-en-3-ol 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:

: 69152-87-0
4-benzyloxycrotonaldehyde

: 156568-08-0
(3S,4R,5R)-3,4-syn-6-(Benzyloxy)-5-((tert-butyldimethylsilyl)oxy)-4-(methoxymethoxy)hex-1-en-3-ol

Guidance literature:: Multi-step reaction with 11 steps

1: 48 percent / Li / tetrahydrofuran / 1.) r.t., 18 h, 2.) -100 deg C, 45 min

2: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) -78 deg C to r.t., then r.t., 0.5 h

3: (-)-chlorodiisopinocampheylborane / tetrahydrofuran / 2 h / -35 °C

4: 82 percent / DMAP, NEt₃ / CH₂Cl₂ / 2 h / Ambient temperature

5: 72 percent / trimethylamine N-oxide / OsO₄ / acetone; H₂O / Ambient temperature

6: 99 percent / imidazole / dimethylformamide / 8 h / Ambient temperature

7: 95 percent / tetrabutylammonium iodide, Hunigs' base / CH₂Cl₂ / 96 h / Ambient temperature

8: 94 percent / diisobutylaluminum hydride / CH₂Cl₂; tetrahydrofuran / -78 °C

9: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) -78 deg C to r.t., then r.t., 0.5 h

10: 84 percent / H₂ / 10percent Pd/C / ethanol / 760 Torr / Ambient temperature

11: CH₂Cl₂; tetrahydrofuran / 0.25 h / -78 °C

With 1H-imidazole; dmap; oxalyl dichloride; trimethylamine-N-oxide; hydrogen; tetra-(n-butyl)ammonium iodide; lithium; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; (-)-diisopinocamphenylborane chloride; palladium on activated charcoal; osmium(VIII) oxide; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo00090a025

Reference yield:

: 133618-96-9
(E)-1-(phenyldimethylsilyl)-4-(benzyloxy)-but-2-en-1-ol

: 156568-08-0
(3S,4R,5R)-3,4-syn-6-(Benzyloxy)-5-((tert-butyldimethylsilyl)oxy)-4-(methoxymethoxy)hex-1-en-3-ol

Guidance literature:: Multi-step reaction with 10 steps

1: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) -78 deg C to r.t., then r.t., 0.5 h

2: (-)-chlorodiisopinocampheylborane / tetrahydrofuran / 2 h / -35 °C

3: 82 percent / DMAP, NEt₃ / CH₂Cl₂ / 2 h / Ambient temperature

4: 72 percent / trimethylamine N-oxide / OsO₄ / acetone; H₂O / Ambient temperature

5: 99 percent / imidazole / dimethylformamide / 8 h / Ambient temperature

6: 95 percent / tetrabutylammonium iodide, Hunigs' base / CH₂Cl₂ / 96 h / Ambient temperature

7: 94 percent / diisobutylaluminum hydride / CH₂Cl₂; tetrahydrofuran / -78 °C

8: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) -78 deg C to r.t., then r.t., 0.5 h

9: 84 percent / H₂ / 10percent Pd/C / ethanol / 760 Torr / Ambient temperature

10: CH₂Cl₂; tetrahydrofuran / 0.25 h / -78 °C

With 1H-imidazole; dmap; oxalyl dichloride; trimethylamine-N-oxide; hydrogen; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; (-)-diisopinocamphenylborane chloride; palladium on activated charcoal; osmium(VIII) oxide; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo00090a025

Reference yield:

: 129921-63-7
(R)-(E)-1-(Acetyloxy)-4-(benzyloxy)-1-(dimethylphenylsilyl)-2-butene

: 156568-08-0
(3S,4R,5R)-3,4-syn-6-(Benzyloxy)-5-((tert-butyldimethylsilyl)oxy)-4-(methoxymethoxy)hex-1-en-3-ol

Guidance literature:: Multi-step reaction with 7 steps

1: 72 percent / trimethylamine N-oxide / OsO₄ / acetone; H₂O / Ambient temperature

2: 99 percent / imidazole / dimethylformamide / 8 h / Ambient temperature

3: 95 percent / tetrabutylammonium iodide, Hunigs' base / CH₂Cl₂ / 96 h / Ambient temperature

4: 94 percent / diisobutylaluminum hydride / CH₂Cl₂; tetrahydrofuran / -78 °C

5: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) -78 deg C to r.t., then r.t., 0.5 h

6: 84 percent / H₂ / 10percent Pd/C / ethanol / 760 Torr / Ambient temperature

7: CH₂Cl₂; tetrahydrofuran / 0.25 h / -78 °C

With 1H-imidazole; oxalyl dichloride; trimethylamine-N-oxide; hydrogen; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; osmium(VIII) oxide; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo00090a025