1-N-acetyl-4-O-<-3',6'-di-O-acetyl-4',8'-anhydro-2',7'-dideoxy-2'-(tosylamino)-D-glycero-α-D-gluco-oct-7'-enopyranos-1'-yl>-5,6-O-cyclohexylidene-1,3-di-N-tosyl-2-deoxystreptamine

Base Information

• Chemical Name: 1-N-acetyl-4-O-<-3',6'-di-O-acetyl-4',8'-anhydro-2',7'-dideoxy-2'-(tosylamino)-D-glycero-α-D-gluco-oct-7'-enopyranos-1'-yl>-5,6-O-cyclohexylidene-1,3-di-N-tosyl-2-deoxystreptamine
• CAS No.: 88970-34-7
• Molecular Formula: C₄₇H₅₇N₃O₁₆S₃
• Molecular Weight: 1016.18

Synonyms:

Chemical Property of 1-N-acetyl-4-O-<-3',6'-di-O-acetyl-4',8'-anhydro-2',7'-dideoxy-2'-(tosylamino)-D-glycero-α-D-gluco-oct-7'-enopyranos-1'-yl>-5,6-O-cyclohexylidene-1,3-di-N-tosyl-2-deoxystreptamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-N-acetyl-4-O-<-3',6'-di-O-acetyl-4',8'-anhydro-2',7'-dideoxy-2'-(tosylamino)-D-glycero-α-D-gluco-oct-7'-enopyranos-1'-yl>-5,6-O-cyclohexylidene-1,3-di-N-tosyl-2-deoxystreptamine

There total 12 articles about 1-N-acetyl-4-O-<-3',6'-di-O-acetyl-4',8'-anhydro-2',7'-dideoxy-2'-(tosylamino)-D-glycero-α-D-gluco-oct-7'-enopyranos-1'-yl>-5,6-O-cyclohexylidene-1,3-di-N-tosyl-2-deoxystreptamine 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:

C47H64N4O12S3 (91613-41-1) → 1-N-acetyl-4-O-<-3',6'-di-O-acetyl-4',8'-anhydro-2',7'-dideoxy-2'-(tosylamino)-D-glycero-α-D-gluco-oct-7'-enopyranos-1'-yl>-5,6-O-cyclohexylidene-1,3-di-N-tosyl-2-deoxystreptamine (88970-34-7,91685-46-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 47.1 percent / m-chloroperbenzoic acid / CHCl₃ / 1 h / Ambient temperature

2: 75 percent / N,N-diisopropylethylamine, benzoyl chloride / acetone / 1) RT, 3 min.; 2) 40 deg C, 10 min.

3: 41 percent / tetrahydrofuran / 1) under argon, RT, 15 min.; 2) 60 deg C, 30 min.

4: triethylamine, tosyl chloride / acetonitrile / 12 h / Ambient temperature

5: 95 mg / pyridine / 19 h / 40 °C

With benzoyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; p-toluenesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; pyridine; chloroform; acetone; acetonitrile;

DOI:10.1246/bcsj.57.529

Reference yield:

4-O-<3',4'-O-cyclohexylidene-2'-deoxy-(tosylamino)-α-D-gluco-hexodialdo-1',5'-pyranosyl>-5,6-O-cyclohexylidene-1,3-di-N-tosyl-2-deoxystreptamine (88970-29-0) → 1-N-acetyl-4-O-<-3',6'-di-O-acetyl-4',8'-anhydro-2',7'-dideoxy-2'-(tosylamino)-D-glycero-α-D-gluco-oct-7'-enopyranos-1'-yl>-5,6-O-cyclohexylidene-1,3-di-N-tosyl-2-deoxystreptamine (88970-34-7,91685-46-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 41 percent / tetrahydrofuran / 1) under argon, RT, 15 min.; 2) 60 deg C, 30 min.

2: triethylamine, tosyl chloride / acetonitrile / 12 h / Ambient temperature

3: 95 mg / pyridine / 19 h / 40 °C

With triethylamine; p-toluenesulfonyl chloride; In tetrahydrofuran; pyridine; acetonitrile;

DOI:10.1246/bcsj.57.529

Reference yield:

3',4':5,6-di-O-cyclohexylidene-6',6'-di-N-methyl-1,2',3-tri-N-tosylneamine 6'-N-oxide (88970-28-9) → 1-N-acetyl-4-O-<-3',6'-di-O-acetyl-4',8'-anhydro-2',7'-dideoxy-2'-(tosylamino)-D-glycero-α-D-gluco-oct-7'-enopyranos-1'-yl>-5,6-O-cyclohexylidene-1,3-di-N-tosyl-2-deoxystreptamine (88970-34-7,91685-46-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / N,N-diisopropylethylamine, benzoyl chloride / acetone / 1) RT, 3 min.; 2) 40 deg C, 10 min.

2: 41 percent / tetrahydrofuran / 1) under argon, RT, 15 min.; 2) 60 deg C, 30 min.

3: triethylamine, tosyl chloride / acetonitrile / 12 h / Ambient temperature

4: 95 mg / pyridine / 19 h / 40 °C

With benzoyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; p-toluenesulfonyl chloride; In tetrahydrofuran; pyridine; acetone; acetonitrile;

DOI:10.1246/bcsj.57.529

upstream raw materials:

acetic anhydride

p-toluenesulfonyl chloride

C₄₇H₆₄N₄O₁₂S₃

4-O-<3',4'-O-cyclohexylidene-2'-deoxy-(tosylamino)-α-D-gluco-hexodialdo-1',5'-pyranosyl>-5,6-O-cyclohexylidene-1,3-di-N-tosyl-2-deoxystreptamine

Downstream raw materials:

aprosamine tetrahydrochloride trihydrate

4-O-<(8'S)-7'-N,6'-O-carbonyl-2',3',7'-trideoxy-8'-O-methyl-7'-(methylamino)-2'-(tosylamino)-D-glycero-α-D-allo-octodialdo-1',5':8',4'-dipyranos-1'-yl>-5,6-O-cyclohexylidene-1,3-di-N-tosyl-2-deoxystreptamine

4-O-<(8'S)-7'--2',7'-dideoxy-8'-O-methyl-2'-(tosylamino)-D-threo-α-D-gluco-octodialdo-1',5':8',4'-dipyranos-1'-yl>-5,6-O-cyclohexylidene-1,3-di-N-tosyl-2-deoxystreptamine

4-O-<(8'S)-7'--2',7'-dideoxy-3',6'-di-O-mesyl-8'-O-methyl-2'-(tosylamino)-D-threo-α-D-gluco-octodialdo-1',5':8',4'-dipyranos-1'-yl>-5,6-O-cyclohexylidene-1,3-di-N-tosyl-2-deoxystreptamine

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