1-O-[2-deoxy-2-(N-tert-butyloxycarbonyl-S-acetyl-L-cysteinyl)amino-α-D-glucopyranosyl]-D-myo-inositol

Base Information

• Chemical Name: 1-O-[2-deoxy-2-(N-tert-butyloxycarbonyl-S-acetyl-L-cysteinyl)amino-α-D-glucopyranosyl]-D-myo-inositol
• CAS No.: 1228173-37-2
• Molecular Formula: C₂₂H₃₈N₂O₁₄S
• Molecular Weight: 586.615
• Mol file: 1228173-37-2.mol

Synonyms:1-O-[2-deoxy-2-(N-tert-butyloxycarbonyl-S-acetyl-L-cysteinyl)amino-α-D-glucopyranosyl]-D-myo-inositol

Chemical Property of 1-O-[2-deoxy-2-(N-tert-butyloxycarbonyl-S-acetyl-L-cysteinyl)amino-α-D-glucopyranosyl]-D-myo-inositol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-O-[2-deoxy-2-(N-tert-butyloxycarbonyl-S-acetyl-L-cysteinyl)amino-α-D-glucopyranosyl]-D-myo-inositol

There total 3 articles about 1-O-[2-deoxy-2-(N-tert-butyloxycarbonyl-S-acetyl-L-cysteinyl)amino-α-D-glucopyranosyl]-D-myo-inositol 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: 80.0%

C12H23NO10*C2H4O2 + N-(tert-butoxycarbonyl)-S-acetyl-L-cysteine (21948-02-7) → 1-O-[2-deoxy-2-(N-tert-butyloxycarbonyl-S-acetyl-L-cysteinyl)amino-α-D-glucopyranosyl]-D-myo-inositol (1228173-37-2)

Guidance literature:

C₁₂H₂₃NO₁₀*C₂H₄O₂;

N-(tert-butoxycarbonyl)-S-acetyl-L-cysteine; With N-ethyl-N,N-diisopropylamine; ethyl cyanoglyoxylate-2-oxime; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.3762/bjoc.12.35

Reference yield: 78.0%

1-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol hydrochloride (1228173-30-5) + N-(tert-butoxycarbonyl)-S-acetyl-L-cysteine (21948-02-7) → 1-O-[2-deoxy-2-(N-tert-butyloxycarbonyl-S-acetyl-L-cysteinyl)amino-α-D-glucopyranosyl]-D-myo-inositol (1228173-37-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 4 - 20 ℃; Inert atmosphere;

DOI:10.1021/ol202218n

Reference yield:

1-O-[2-azido-3-O-(4-bromobenzyl)-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2,4,5,6-tetra-O-benzyl-D-myo-inositol (1334379-58-6) → 1-O-[2-deoxy-2-(N-tert-butyloxycarbonyl-S-acetyl-L-cysteinyl)amino-α-D-glucopyranosyl]-D-myo-inositol (1228173-37-2)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride; hydrogen; palladium(II) hydroxide / methanol; water / 72 h

2: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 4 - 20 °C / Inert atmosphere

With hydrogenchloride; hydrogen; palladium(II) hydroxide; N-ethyl-N,N-diisopropylamine; HATU; In methanol; water; N,N-dimethyl-formamide;

DOI:10.1021/ol202218n

upstream raw materials:

1-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol hydrochloride

N-(tert-butoxycarbonyl)-S-acetyl-L-cysteine

1-O-[2-azido-3-O-(4-bromobenzyl)-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2,4,5,6-tetra-O-benzyl-D-myo-inositol

Downstream raw materials:

1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-α-D-glucopyranosyl)-D-myo-inositol