methyl 1'-epiacarviosin

Base Information

• Chemical Name: methyl 1'-epiacarviosin
• CAS No.: 140148-00-1
• Molecular Formula: C14H25NO8
• Molecular Weight: 335.3502
• Mol file: 140148-00-1.mol

Synonyms:methyl 1-epiacarviosin;

Chemical Property of methyl 1'-epiacarviosin

Chemical Property:

• Boiling Point: 576.5°Cat760mmHg
• Flash Point: 302.4°C
• PSA: 151.87000
• Density: 1.48g/cm³
• LogP: -3.16790

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of methyl 1'-epiacarviosin

There total 9 articles about methyl 1'-epiacarviosin 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: 100.0%

methyl 4,6-dideoxy-4-<(1R)-(1,5/4,6)-4,5,6-trihydroxy-3-hydroxymethyl-2-cyclohexenyl>amino-α-D-glucopyranoside 2,3:4',7':5',6'-tri-O-isopropylidene derivative (139964-57-1,142561-85-1) → methyl 1'-epiacarviosin (140148-00-1)

Guidance literature:

With acetic acid; at 60 ℃; for 2h;

DOI:10.1016/0008-6215(92)80025-V

Reference yield:

(1S,2R,9S,10S)-9-amino-4,4,12,12-tetramethyl-3,5,11,13-tetraoxatricyclo[8.3.0.02,7]tridec-7-ene (132016-22-9) → methyl 1'-epiacarviosin (140148-00-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 51 percent / propan-2-ol / 45 h / 120 °C

2: 50 percent / pyridine / 37 h / 0 °C

3: 36 percent / p-toluenesulfonic acid monohydrate / dimethylformamide / 16 h / Ambient temperature

4: 94 percent / NaI / dimethylformamide / 2.5 h / 100 °C

5: 91 percent / lithium triethylborohydride / tetrahydrofuran / 1 h / 0 °C

6: 100 percent / aq. 70percent AcOH / 2 h / 60 °C

With pyridine; lithium triethylborohydride; toluene-4-sulfonic acid; acetic acid; sodium iodide; In tetrahydrofuran; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1016/0008-6215(92)80025-V

Reference yield:

methyl 4-deoxy-4-<(1R)-(1,5/4,6)-4,5,6-trihydroxy-3-hydroxymethyl-2-cyclohexenyl>amino-α-D-glucopyranoside 4',7':5',6'-di-O-isopropylidene derivative (131922-33-3,140148-04-5) → methyl 1'-epiacarviosin (140148-00-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 50 percent / pyridine / 37 h / 0 °C

2: 36 percent / p-toluenesulfonic acid monohydrate / dimethylformamide / 16 h / Ambient temperature

3: 94 percent / NaI / dimethylformamide / 2.5 h / 100 °C

4: 91 percent / lithium triethylborohydride / tetrahydrofuran / 1 h / 0 °C

5: 100 percent / aq. 70percent AcOH / 2 h / 60 °C

With pyridine; lithium triethylborohydride; toluene-4-sulfonic acid; acetic acid; sodium iodide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(92)80025-V

upstream raw materials:

methyl 4,6-dideoxy-4-<(1R)-(1,5/4,6)-4,5,6-trihydroxy-3-hydroxymethyl-2-cyclohexenyl>amino-α-D-glucopyranoside 2,3:4',7':5',6'-tri-O-isopropylidene derivative

(1S,2R,9S,10S)-9-amino-4,4,12,12-tetramethyl-3,5,11,13-tetraoxatricyclo[8.3.0.0^2,7]tridec-7-ene

methyl 4-deoxy-4-<(1R)-(1,5/4,6)-4,5,6-trihydroxy-3-hydroxymethyl-2-cyclohexenyl>amino-α-D-glucopyranoside 4',7':5',6'-di-O-isopropylidene derivative

methyl 4,6-dideoxy-4-<(1R)-(1,5/4,6)-4,5,6-trihydroxy-3-hydroxymethyl-2-cyclohexenyl>amino-6-iodo-α-D-glucopyranoside 2,3:4',7':5',6'-tri-O-isopropylidene derivative

Downstream raw materials:

methyl 1'-epiacarviosin hexaacetate

Refernces