[N'-((3R,5R)-3,6-Diazido-5-benzyloxymethoxy-hexanoyl)-N-methyl-hydrazino]-acetic acid benzyl ester

Base Information

• Chemical Name: [N'-((3R,5R)-3,6-Diazido-5-benzyloxymethoxy-hexanoyl)-N-methyl-hydrazino]-acetic acid benzyl ester
• CAS No.: 119138-84-0
• Molecular Formula: C₂₄H₃₀N₈O₅
• Molecular Weight: 510.553
• Mol file: 119138-84-0.mol

Synonyms:[N'-((3R,5R)-3,6-Diazido-5-benzyloxymethoxy-hexanoyl)-N-methyl-hydrazino]-acetic acid benzyl ester

Chemical Property of [N'-((3R,5R)-3,6-Diazido-5-benzyloxymethoxy-hexanoyl)-N-methyl-hydrazino]-acetic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [N'-((3R,5R)-3,6-Diazido-5-benzyloxymethoxy-hexanoyl)-N-methyl-hydrazino]-acetic acid benzyl ester

There total 14 articles about [N'-((3R,5R)-3,6-Diazido-5-benzyloxymethoxy-hexanoyl)-N-methyl-hydrazino]-acetic acid benzyl ester 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: 63.0%

benzyl 2-(1-methylhydrazinyl)acetate (55501-33-2) + (3R,5R)-3,6-Diazido-5-benzyloxymethoxy-hexanoic acid (119138-85-1) → [N'-((3R,5R)-3,6-Diazido-5-benzyloxymethoxy-hexanoyl)-N-methyl-hydrazino]-acetic acid benzyl ester (119138-84-0)

Guidance literature:

With chloroformic acid ethyl ester; triethylamine; In toluene; at -5 ℃;

DOI:10.1016/S0040-4039(00)86063-3

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → [N'-((3R,5R)-3,6-Diazido-5-benzyloxymethoxy-hexanoyl)-N-methyl-hydrazino]-acetic acid benzyl ester (119138-84-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / ⁱPr₂NEt / CH₂Cl₂ / Ambient temperature

2: 94 percent / ⁿBu₄NF / tetrahydrofuran

3: 67 percent / NaIO₄ / RuCl₃ / acetonitrile; CCl₄; H₂O / Ambient temperature

4: 63 percent / ClCO₂Et, NEt₃ / toluene / -5 °C

With sodium periodate; tetrabutyl ammonium fluoride; chloroformic acid ethyl ester; triethylamine; N-ethyl-N,N-diisopropylamine; ruthenium trichloride; In tetrahydrofuran; tetrachloromethane; dichloromethane; water; toluene; acetonitrile;

DOI:10.1016/S0040-4039(00)86063-3

Reference yield:

(R)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-butane-1,3-diol → [N'-((3R,5R)-3,6-Diazido-5-benzyloxymethoxy-hexanoyl)-N-methyl-hydrazino]-acetic acid benzyl ester (119138-84-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 89 percent / DMAP, NEt₃ / CH₂Cl₂ / Ambient temperature

2: 100 percent / tetrahydrofuran / 0 °C

3: 99 percent / NaN₃ / 15-crown-5 / dimethylformamide / 50 °C

4: 87 percent / CuCl₂*2H₂O / ethanol / Ambient temperature

5: 92 percent / pyridine / -20 °C

6: 91 percent / NaN₃ / 15-crown-5 / dimethylformamide / 50 °C

7: 93 percent / ⁱPr₂NEt / CH₂Cl₂ / Ambient temperature

8: 94 percent / ⁿBu₄NF / tetrahydrofuran

9: 67 percent / NaIO₄ / RuCl₃ / acetonitrile; CCl₄; H₂O / Ambient temperature

10: 63 percent / ClCO₂Et, NEt₃ / toluene / -5 °C

With pyridine; dmap; sodium periodate; sodium azide; tetrabutyl ammonium fluoride; chloroformic acid ethyl ester; triethylamine; N-ethyl-N,N-diisopropylamine; ruthenium trichloride; 15-crown-5; In tetrahydrofuran; tetrachloromethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/S0040-4039(00)86063-3

upstream raw materials:

benzyl 2-(1-methylhydrazinyl)acetate

(3R,5R)-3,6-Diazido-5-benzyloxymethoxy-hexanoic acid

Benzyloxymethyl chloride

[(2S,3S)-3-((R)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethyl)-oxiranyl]-methanol

Downstream raw materials:

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