2-benzyloxycarbonylamino-2-deoxy-3,4-O-isopropylidene-D-erythronamide

Base Information

• Chemical Name: 2-benzyloxycarbonylamino-2-deoxy-3,4-O-isopropylidene-D-erythronamide
• CAS No.: 115802-85-2
• Molecular Formula: C₁₅H₂₀N₂O₅
• Molecular Weight: 308.334
• Mol file: 115802-85-2.mol

Synonyms:2-benzyloxycarbonylamino-2-deoxy-3,4-O-isopropylidene-D-erythronamide

Chemical Property of 2-benzyloxycarbonylamino-2-deoxy-3,4-O-isopropylidene-D-erythronamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-benzyloxycarbonylamino-2-deoxy-3,4-O-isopropylidene-D-erythronamide

There total 7 articles about 2-benzyloxycarbonylamino-2-deoxy-3,4-O-isopropylidene-D-erythronamide 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:

(Z)-(4S)-2,2-dimethoxy-4-<2'-<4''-(methylphenyl)thio>-2'-nitroethenyl>-1,3-dioxolane (150640-12-3) → 2-benzyloxycarbonylamino-2-deoxy-3,4-O-isopropylidene-D-erythronamide (115802-85-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 60 percent / t-BuOOLi / tetrahydrofuran / 2 h / -78 °C

2: aq. NH₃ / CH₂Cl₂ / 2 h / Ambient temperature

3: 0.5 h / Ambient temperature

4: ammonia

With ammonium hydroxide; lithium tert-butyl hydroperoxide; ammonia; In tetrahydrofuran; dichloromethane;

DOI:10.1039/c39930000889

Reference yield:

(2'S,3'S,4R)-2,2-dimethyl-4-<3'-<(4''-methylphenyl)thio>-3'-nitrooxiran-2'-yl>-1,3-dioxolane (150640-13-4) → 2-benzyloxycarbonylamino-2-deoxy-3,4-O-isopropylidene-D-erythronamide (115802-85-2)

Guidance literature:

Multi-step reaction with 3 steps

1: aq. NH₃ / CH₂Cl₂ / 2 h / Ambient temperature

2: 0.5 h / Ambient temperature

3: ammonia

With ammonium hydroxide; ammonia; In dichloromethane;

DOI:10.1039/c39930000889

Reference yield:

2,3-isopropylidene-glyceraldehyde (15186-48-8) → 2-benzyloxycarbonylamino-2-deoxy-3,4-O-isopropylidene-D-erythronamide (115802-85-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) t-BuOK, 2.) MeSO₂Cl, NEt₃ / 1.) t-BuOH, THF, 0 deg C, 2.) t-BuOH, THF, from -78 deg C to 0 deg C

2: 60 percent / t-BuOOLi / tetrahydrofuran / 2 h / -78 °C

3: aq. NH₃ / CH₂Cl₂ / 2 h / Ambient temperature

4: 0.5 h / Ambient temperature

5: ammonia

With ammonium hydroxide; potassium tert-butylate; lithium tert-butyl hydroperoxide; ammonia; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1039/c39930000889

upstream raw materials:

S-(4''-methylphenyl) (2'R,4S)-2'-<(benzyloxycarbonyl)amino>-2'-(2,2-dimethyl-1,3-dioxolan-4-yl)ethanethioate

trimethylsilyl cyanide

benzyl chloroformate

2,3-isopropylidene-glyceraldehyde

Downstream raw materials:

2-benzyloxycarbonylamino-2-deoxy-D-erythronamide

(2R,3S)-2-(N-benzyloxycarbonyl)amino-3-hydroxy-4-butanolide