(3R,4R,5R)-N-benzyloxycarbonyl-5-allylamino-3,4,6-tribenzyloxy-hex-1-ene

Base Information

Chemical Name:(3R,4R,5R)-N-benzyloxycarbonyl-5-allylamino-3,4,6-tribenzyloxy-hex-1-ene
CAS No.:724705-47-9
Molecular Formula:C₃₈H₄₁NO₅
Molecular Weight:591.747
Hs Code.:

Synonyms:(3R,4R,5R)-N-benzyloxycarbonyl-5-allylamino-3,4,6-tribenzyloxy-hex-1-ene

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3R,4R,5R)-N-benzyloxycarbonyl-5-allylamino-3,4,6-tribenzyloxy-hex-1-ene

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Technology Process of (3R,4R,5R)-N-benzyloxycarbonyl-5-allylamino-3,4,6-tribenzyloxy-hex-1-ene

There total 8 articles about (3R,4R,5R)-N-benzyloxycarbonyl-5-allylamino-3,4,6-tribenzyloxy-hex-1-ene 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: 88.0%

: 106-95-6
allyl bromide

: 160925-98-4
benzyl [(2R,3R,4R)-1,3,4-tris(benzyloxy)hex-5-en-2-yl]carbamate

: 724705-47-9
(3R,4R,5R)-N-benzyloxycarbonyl-5-allylamino-3,4,6-tribenzyloxy-hex-1-ene

Guidance literature:: With sodium hydride; In tetrahydrofuran; at 0 ℃;
DOI:10.1055/s-0035-1562438

Reference yield:

: 366815-69-2
(3S,4R)-1,3,4-Tris-benzyloxy-hept-6-en-2-one

: 724705-47-9
(3R,4R,5R)-N-benzyloxycarbonyl-5-allylamino-3,4,6-tribenzyloxy-hex-1-ene

Guidance literature:: Multi-step reaction with 2 steps

1: 35 percent / NaBH(OAc)3; AcOH / CH₂Cl₂ / 36 h / 40 °C

2: 91 percent / aq. KHCO₃ / ethyl acetate / 6 h / 20 °C

With sodium tris(acetoxy)borohydride; potassium hydrogencarbonate; acetic acid; In dichloromethane; ethyl acetate;
DOI:10.1039/b402542c

Reference yield:

: 137820-47-4
(3R,4R,5S)-5-hydroxy-3,4,6-tribenzyloxy-1-hexene

: 724705-47-9
(3R,4R,5R)-N-benzyloxycarbonyl-5-allylamino-3,4,6-tribenzyloxy-hex-1-ene

Guidance literature:: Multi-step reaction with 4 steps

1.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / -20 - 20 °C / Inert atmosphere

2.1: methylamine / water / 1.5 h / 50 °C

3.1: triethylamine / dichloromethane / 0.08 h / 0 °C

3.2: 0 - 20 °C

4.1: sodium hydride / tetrahydrofuran / 0 °C

With di-isopropyl azodicarboxylate; sodium hydride; triethylamine; triphenylphosphine; methylamine; In tetrahydrofuran; dichloromethane; water; 1.1: |Mitsunobu Displacement;
DOI:10.1055/s-0035-1562438