(3R,4S)-4-((S)-1-Benzyloxymethyl-allylamino)-1-(4-methoxy-benzyloxy)-hex-5-en-3-ol

Base Information

Chemical Name:(3R,4S)-4-((S)-1-Benzyloxymethyl-allylamino)-1-(4-methoxy-benzyloxy)-hex-5-en-3-ol
CAS No.:618384-48-8
Molecular Formula:C₂₅H₃₃NO₄
Molecular Weight:411.541
Hs Code.:

Synonyms:(3R,4S)-4-((S)-1-Benzyloxymethyl-allylamino)-1-(4-methoxy-benzyloxy)-hex-5-en-3-ol

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Chemical Property of (3R,4S)-4-((S)-1-Benzyloxymethyl-allylamino)-1-(4-methoxy-benzyloxy)-hex-5-en-3-ol

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Technology Process of (3R,4S)-4-((S)-1-Benzyloxymethyl-allylamino)-1-(4-methoxy-benzyloxy)-hex-5-en-3-ol

There total 7 articles about (3R,4S)-4-((S)-1-Benzyloxymethyl-allylamino)-1-(4-methoxy-benzyloxy)-hex-5-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: 98.0%

: 97682-96-7,99726-01-9,127505-65-1
(2S)-1-(phenylmethoxy)but-3-en-2-ylamine

: 459870-75-8
6-(4-methoxyphenyl)methoxy-3,4-epoxy-1-hexene

: 618384-48-8
(3R,4S)-4-((S)-1-Benzyloxymethyl-allylamino)-1-(4-methoxy-benzyloxy)-hex-5-en-3-ol

Guidance literature:: With lithium trifluoromethanesulfonate; In acetonitrile; at 120 ℃; for 72h;
DOI:10.1021/jo034914q

Reference yield:

: 146916-76-9
5-(4-methoxyphenyl)methoxy-2-pentyn-1-ol

: 618384-48-8
(3R,4S)-4-((S)-1-Benzyloxymethyl-allylamino)-1-(4-methoxy-benzyloxy)-hex-5-en-3-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 89 percent / Red-Al / tetrahydrofuran; toluene / 4 h / 20 °C

2: T-BuOOH; CaH₂; D-(-)-diisopropyl tartrate / silica gel; Ti(O-i-Pr)4 / CH₂Cl₂ / 24 h / -20 °C

3: Et₃N; DMSO; (COCl)2 / CH₂Cl₂ / 0.42 h / -60 - 20 °C

4: 1.51 g / potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 2 h / -10 °C

5: 98 percent / lithium triflate / acetonitrile / 72 h / 120 °C

With tert.-butylhydroperoxide; calcium hydride; oxalyl dichloride; potassium hexamethylsilazane; lithium trifluoromethanesulfonate; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; titanium(IV) isopropylate; silica gel; In tetrahydrofuran; dichloromethane; toluene; acetonitrile; 3: Swern oxidation / 4: Wittig olefination;
DOI:10.1021/jo034914q

Reference yield:

: 158817-21-1
(E)-5-(4-methoxybenzyloxy)pent-2-en-1-ol

: 618384-48-8
(3R,4S)-4-((S)-1-Benzyloxymethyl-allylamino)-1-(4-methoxy-benzyloxy)-hex-5-en-3-ol

Guidance literature:: Multi-step reaction with 4 steps

1: T-BuOOH; CaH₂; D-(-)-diisopropyl tartrate / silica gel; Ti(O-i-Pr)4 / CH₂Cl₂ / 24 h / -20 °C

2: Et₃N; DMSO; (COCl)2 / CH₂Cl₂ / 0.42 h / -60 - 20 °C

3: 1.51 g / potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 2 h / -10 °C

4: 98 percent / lithium triflate / acetonitrile / 72 h / 120 °C

With tert.-butylhydroperoxide; calcium hydride; oxalyl dichloride; potassium hexamethylsilazane; lithium trifluoromethanesulfonate; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; triethylamine; titanium(IV) isopropylate; silica gel; In tetrahydrofuran; dichloromethane; toluene; acetonitrile; 2: Swern oxidation / 3: Wittig olefination;
DOI:10.1021/jo034914q