N-((1S,4R,5S,6S)-4,5,6-Trihydroxy-3-hydroxymethyl-cyclohex-2-enyl)-acetamide

Base Information

• Chemical Name: N-((1S,4R,5S,6S)-4,5,6-Trihydroxy-3-hydroxymethyl-cyclohex-2-enyl)-acetamide
• CAS No.: 84270-00-8
• Molecular Formula: C₉H₁₅NO₅
• Molecular Weight: 217.222
• Mol file: 84270-00-8.mol

Synonyms:N-((1S,4R,5S,6S)-4,5,6-Trihydroxy-3-hydroxymethyl-cyclohex-2-enyl)-acetamide

Chemical Property of N-((1S,4R,5S,6S)-4,5,6-Trihydroxy-3-hydroxymethyl-cyclohex-2-enyl)-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-((1S,4R,5S,6S)-4,5,6-Trihydroxy-3-hydroxymethyl-cyclohex-2-enyl)-acetamide

There total 5 articles about N-((1S,4R,5S,6S)-4,5,6-Trihydroxy-3-hydroxymethyl-cyclohex-2-enyl)-acetamide 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: 96.0%

valienamine (74645-52-6) → N-((1S,4R,5S,6S)-4,5,6-Trihydroxy-3-hydroxymethyl-cyclohex-2-enyl)-acetamide (84270-00-8)

Guidance literature:

With sodium methylate; In methanol; for 0.5h; Ambient temperature;

DOI:10.1016/0008-6215(88)84151-X

Reference yield:

Benzoic acid (1R,2S,3R,4S,5S)-2,4-diacetoxy-5-acetylamino-3-benzyloxy-1-hydroxy-cyclohexylmethyl ester (119951-78-9) → N-((1S,4R,5S,6S)-4,5,6-Trihydroxy-3-hydroxymethyl-cyclohex-2-enyl)-acetamide (84270-00-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / SOCl₂ / pyridine / 0.25 h / 2 °C

2: 1.) 1percent NaOH; 2.) Na / 1.) MeOH; 2.) liq. NH₃

With sodium hydroxide; thionyl chloride; sodium; In pyridine;

Reference yield:

Benzoic acid (1R,2S,3R,4S,5S)-2,4-diacetoxy-5-acetylamino-3-benzyloxy-1-hydroxy-6-nitro-cyclohexylmethyl ester (119951-77-8,120053-41-0) → N-((1S,4R,5S,6S)-4,5,6-Trihydroxy-3-hydroxymethyl-cyclohex-2-enyl)-acetamide (84270-00-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 60 percent / n-Bu3SnH, α-α'azobis-iso-butyronitrile / benzene

2: 89 percent / SOCl₂ / pyridine / 0.25 h / 2 °C

3: 1.) 1percent NaOH; 2.) Na / 1.) MeOH; 2.) liq. NH₃

With sodium hydroxide; thionyl chloride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium; In pyridine; benzene;

upstream raw materials:

Benzoic acid (3S,4S,5S,6R)-4,6-diacetoxy-3-acetylamino-5-benzyloxy-cyclohex-1-enylmethyl ester

Benzoic acid (1R,2S,3R,4S,5S)-2,4-diacetoxy-5-acetylamino-3-benzyloxy-1-hydroxy-cyclohexylmethyl ester

Benzoic acid (1R,2S,3R,4S,5S)-2,4-diacetoxy-5-acetylamino-3-benzyloxy-1-hydroxy-6-nitro-cyclohexylmethyl ester

Benzoic acid (1R,2S,3R,4S,5R,6R)-2,4,5-triacetoxy-3-benzyloxy-1-hydroxy-6-nitro-cyclohexylmethyl ester

Downstream raw materials:

(1L)-(1,3,4/2)-4-acetamido-1,2,3-tri-O-acetyl-4-[(acetoxy)methyl]cyclohex-5-ene-1,2,3-triol

valienamine

valienamine

DL-(1,2,3,5,6/4)-6-acetamido-2-C-acetoxymethyl-3,4,5-tri-O-acetyl-1,2-anhydro-1,2,3,4,5-cyclohexanepentol