Methyl 6-amino-6,8-dideoxy-1-thio-D-erythro-α-D-galacto-octopyranoside

Base Information

• Chemical Name: Methyl 6-amino-6,8-dideoxy-1-thio-D-erythro-α-D-galacto-octopyranoside
• CAS No.: 14810-93-6
• Molecular Formula: C9H19NO5S
• Molecular Weight: 253.32
• Mol file: 14810-93-6.mol

Synonyms:Methyl 1-thiolincosaminide;Methyl 6-amino-6,8-dideoxy-1-thio-D-erythro-α-D-galacto-octopyranoside;Methyl thiolincosaminide;Methyl α-thiolincosaminide

Chemical Property of Methyl 6-amino-6,8-dideoxy-1-thio-D-erythro-α-D-galacto-octopyranoside

Chemical Property:

• Melting Point: 185-188°C (dec.)
• Boiling Point: 510.7±50.0 °C(Predicted)
• PKA: 12.63±0.45(Predicted)
• PSA: 141.47000
• Density: 1.42±0.1 g/cm3(Predicted)
• LogP: -1.43460
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly, Heated, Sonicated), Methanol (Slightly), Water (Slightly, Sonica

Purity/Quality:

99%, ^*data from raw suppliers

Methyl 1-thiolincosaminide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Intermediate in the production of biosynthetic antibiotics

Technology Process of Methyl 6-amino-6,8-dideoxy-1-thio-D-erythro-α-D-galacto-octopyranoside

There total 16 articles about Methyl 6-amino-6,8-dideoxy-1-thio-D-erythro-α-D-galacto-octopyranoside 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: 91.0%

Methyl 6-Acetamido-6,8-dideoxy-1-thio-D-erythro-α-D-galacto-octopyranoside (6982-20-3) → Methyl 6-Amino-6,8-dideoxy-1-thio-D-erythro-α-D-galacto-octopyranoside (14810-93-6)

Guidance literature:

With hydrazine hydrate; for 3h; Heating;

DOI:10.1021/jo00292a044

Reference yield: 89.0%

C16H23NO5S → Methyl 6-Amino-6,8-dideoxy-1-thio-D-erythro-α-D-galacto-octopyranoside (14810-93-6)

Guidance literature:

C₁₆H₂₃NO₅S; With ammonia; sodium; In tetrahydrofuran; at -78 ℃; Inert atmosphere; Sealed tube;

With acetic acid; zinc; In water; at 35 ℃; for 3h; Inert atmosphere;

DOI:10.1021/jacs.1c03536

Reference yield: 88.0%

lincomycin hydrochloride (859-18-7) → Methyl 6-Amino-6,8-dideoxy-1-thio-D-erythro-α-D-galacto-octopyranoside (14810-93-6)

Guidance literature:

With water; at 100 ℃; for 72h; Inert atmosphere;

DOI:10.1021/jacs.1c03536

upstream raw materials:

Methyl 6-Acetamido-6,8-dideoxy-1-thio-D-erythro-α-D-galacto-octopyranoside

methyl (E)-2,3-di-O-benzyl-6,7,8-trideoxy-α-D-galacto-oct-6-enopyranoside

(2S,3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-((2R,3R)-3-methyl-oxiranyl)-tetrahydro-pyran-3-ol

Methyl 2,3-Bis-O-(phenylmethyl)-6,8-dideoxy-7,6-<2-(N,N-dimethylamino)-1-oxa-3-azaprop-2-eno>-D-erythro-α-D-galacto-octopyranoside

Downstream raw materials:

C₂₉H₅₇NO₇SSi₄

methyl 6-amino-7(S)-chloro-6,7,8-trideoxy-1-thio-L-threo-α-D-galacto-octopyranoside

methyl (7S)-6-N-((2′S,4′R)-4′-(n-butyl)piperidine-2′-carbonyl)-7-deoxy-7-(4-(pyrimidin-5-yl)phenylthio)-α-thiolincosaminide

methyl (7S)-6-N-((2′S,4′R)-4′-(n-propyl)piperidine-2′-carbonyl)-7-deoxy-7-(4-(pyrimidin-5-yl)phenylthio)-α-thiolincosaminide

Refernces

• 1、 Mason, Jeremy D.,Myers, Andrew G.,Pote, Aditya R.,Terwilliger, Daniel W.. "Practical Gram-Scale Synthesis of Iboxamycin, a Potent Antibiotic Candidate". supporting information. p. 11019 - 11025. Retrieved 2021/08/03.
• 2、 Collin, Marie-Pierre,Hobbie, Sven N.,Boettger, Erik C.,Vasella, Andrea. "Synthesis of 1,2,3-triazole analogues of lincomycin". scheme or table. p. 1838 - 1848. Retrieved 2009/02/07.