[1-[(4R,5R)-5-((R)-1-Benzyloxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-eth-(E)-ylidene]-hydrazine

Base Information

• Chemical Name: [1-[(4R,5R)-5-((R)-1-Benzyloxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-eth-(E)-ylidene]-hydrazine
• CAS No.: 124928-81-0
• Molecular Formula: C₁₈H₂₈N₂O₃
• Molecular Weight: 320.432

Synonyms:

Chemical Property of [1-[(4R,5R)-5-((R)-1-Benzyloxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-eth-(E)-ylidene]-hydrazine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [1-[(4R,5R)-5-((R)-1-Benzyloxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-eth-(E)-ylidene]-hydrazine

There total 16 articles about [1-[(4R,5R)-5-((R)-1-Benzyloxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-eth-(E)-ylidene]-hydrazine 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:

5-O-benzyl-1,6,7-trideoxy-3,4-O-isopropylidene-4-C-methyl-keto-D-arabino-2-heptulose (105544-93-2) → [1-[(4R,5R)-5-((R)-1-Benzyloxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-eth-(E)-ylidene]-hydrazine (124928-81-0)

Guidance literature:

With hydrazine hydrate; triethylamine; In ethanol; at 70 ℃; for 1h;

DOI:10.1016/S0040-4039(00)84382-8

Reference yield:

2,3-O-isopropylidene-D-ribofuranose (67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1,4099-88-1) → [1-[(4R,5R)-5-((R)-1-Benzyloxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-eth-(E)-ylidene]-hydrazine (124928-81-0)

Guidance literature:

Multi-step reaction with 15 steps

1: 73 percent / diethyl ether / 3 h / Ambient temperature

2: NaIO₄ / acetone; H₂O / 2 h / Ambient temperature

3: LiALH₄ / tetrahydrofuran / 2 h / Ambient temperature

4: imidasole / dimethylformamide / 1 h / Ambient temperature

5: 95 percent / PCC, 3A molecular sieves / CH₂Cl₂ / 2 h / Ambient temperature

6: 94 percent / tetrahydrofuran / 2 h / Ambient temperature

7: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C, 2.) from -78 deg C to room temp.

8: diethyl ether / 1.5 h / Ambient temperature

9: 55 percent / NaH / tetrahydrofuran / 4 h / Ambient temperature

10: 95 percent / FeCl₃ / acetone / 1 h / 29 °C

11: 92 percent / (n-Bu)4NF / tetrahydrofuran

12: NaIO₄ / acetone; H₂O / 2 h / Ambient temperature

13: diethyl ether / 3 h / Ambient temperature

14: PCC, 3A molecular sieves / CH₂Cl₂ / 2 h / Ambient temperature

15: NH₂NH₂*H₂O, Et₃N / ethanol / 1 h / 70 °C

With 1H-imidazole; sodium periodate; lithium aluminium tetrahydride; dimethylsulfide; 3 A molecular sieve; tetrabutyl ammonium fluoride; iron(III) chloride; sodium hydride; ozone; hydrazine hydrate; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4039(00)84382-8

Reference yield:

(S)-1-((4S,5R)-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl)ethanol (93223-61-1,114296-87-6,117557-98-9,124990-87-0) → [1-[(4R,5R)-5-((R)-1-Benzyloxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-eth-(E)-ylidene]-hydrazine (124928-81-0)

Guidance literature:

Multi-step reaction with 12 steps

1: imidasole / dimethylformamide / 1 h / Ambient temperature

2: 95 percent / PCC, 3A molecular sieves / CH₂Cl₂ / 2 h / Ambient temperature

3: 94 percent / tetrahydrofuran / 2 h / Ambient temperature

4: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C, 2.) from -78 deg C to room temp.

5: diethyl ether / 1.5 h / Ambient temperature

6: 55 percent / NaH / tetrahydrofuran / 4 h / Ambient temperature

7: 95 percent / FeCl₃ / acetone / 1 h / 29 °C

8: 92 percent / (n-Bu)4NF / tetrahydrofuran

9: NaIO₄ / acetone; H₂O / 2 h / Ambient temperature

10: diethyl ether / 3 h / Ambient temperature

11: PCC, 3A molecular sieves / CH₂Cl₂ / 2 h / Ambient temperature

12: NH₂NH₂*H₂O, Et₃N / ethanol / 1 h / 70 °C

With 1H-imidazole; sodium periodate; dimethylsulfide; 3 A molecular sieve; tetrabutyl ammonium fluoride; iron(III) chloride; sodium hydride; ozone; hydrazine hydrate; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4039(00)84382-8

upstream raw materials:

5-O-benzyl-1,6,7-trideoxy-3,4-O-isopropylidene-4-C-methyl-keto-D-arabino-2-heptulose

2,3-O-isopropylidene-D-ribofuranose

(S)-1-((4S,5R)-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl)ethanol

(R)-1-((4R,5S)-5-((S)-1-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethane-1,2-diol

Downstream raw materials:

5-O-benzyl-1,2,6,7-tetradeoxy-2-iodo-3,4-O-isopropylidene-4-C-methyl-D-arabino-1-heptenitol

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