ethyl [benzyl (3-O-benzyl-2,4-O-di-tert-butylsilylene-β-D-glucopyranosyl)uronate]-(1→2)-6-O-acetyl-4-O-benzyl-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside

Base Information

Chemical Name:ethyl [benzyl (3-O-benzyl-2,4-O-di-tert-butylsilylene-β-D-glucopyranosyl)uronate]-(1→2)-6-O-acetyl-4-O-benzyl-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside
CAS No.:1607445-16-8
Molecular Formula:C₅₆H₆₈O₁₂SSi
Molecular Weight:993.3
Hs Code.:

ethyl [benzyl (3-O-benzyl-2,4-O-di-tert-butylsilylene-β-D-glucopyranosyl)uronate]-(1→2)-6-O-acetyl-4-O-benzyl-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside

Synonyms:ethyl [benzyl (3-O-benzyl-2,4-O-di-tert-butylsilylene-β-D-glucopyranosyl)uronate]-(1→2)-6-O-acetyl-4-O-benzyl-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside

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Chemical Property of ethyl [benzyl (3-O-benzyl-2,4-O-di-tert-butylsilylene-β-D-glucopyranosyl)uronate]-(1→2)-6-O-acetyl-4-O-benzyl-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside

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Technology Process of ethyl [benzyl (3-O-benzyl-2,4-O-di-tert-butylsilylene-β-D-glucopyranosyl)uronate]-(1→2)-6-O-acetyl-4-O-benzyl-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside

There total 6 articles about ethyl [benzyl (3-O-benzyl-2,4-O-di-tert-butylsilylene-β-D-glucopyranosyl)uronate]-(1→2)-6-O-acetyl-4-O-benzyl-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside 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: 67.0%

: 1607445-07-7
ethyl 6-O-acetyl-4-O-benzyl-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside

: 1607445-15-7
benzyl (phenyl 3-O-benzyl-2,4-O-di-tert-butylsilylene-1-thio-β-D-glucopyranoside)uronate

: 1607445-16-8
ethyl [benzyl (3-O-benzyl-2,4-O-di-tert-butylsilylene-β-D-glucopyranosyl)uronate]-(1→2)-6-O-acetyl-4-O-benzyl-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside

Guidance literature:: benzyl (phenyl 3-O-benzyl-2,4-O-di-tert-butylsilylene-1-thio-β-D-glucopyranoside)uronate; With Thiobenzophenon; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; toluene; at -60 ℃; for 0.333333h; Molecular sieve;

ethyl 6-O-acetyl-4-O-benzyl-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside; With trifluoromethylsulfonic anhydride; In dichloromethane; toluene; at -60 - 0 ℃; for 2.16h; Molecular sieve;
DOI:10.1016/j.carres.2014.01.022

Reference yield:

: C₁₉H₂₀O₆S

: 1607445-16-8
ethyl [benzyl (3-O-benzyl-2,4-O-di-tert-butylsilylene-β-D-glucopyranosyl)uronate]-(1→2)-6-O-acetyl-4-O-benzyl-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: caesium carbonate / N,N-dimethyl-formamide / 20 °C

2.1: 2,6-dimethylpyridine / 1,2-dichloro-ethane / 72 h / 20 °C / Inert atmosphere

3.1: Thiobenzophenon; 2,4,6-tri-tert-butylpyrimidine / dichloromethane; toluene / 0.33 h / -60 °C / Molecular sieve

3.2: 2.16 h / -60 - 0 °C / Molecular sieve

With 2,6-dimethylpyridine; caesium carbonate; Thiobenzophenon; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.carres.2014.01.022

Reference yield:

: 189144-54-5
phenyl 3-O-benzyl-1-thio-β-D-glucopyranoside

: 1607445-16-8
ethyl [benzyl (3-O-benzyl-2,4-O-di-tert-butylsilylene-β-D-glucopyranosyl)uronate]-(1→2)-6-O-acetyl-4-O-benzyl-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 2 h

2.1: caesium carbonate / N,N-dimethyl-formamide / 20 °C

3.1: 2,6-dimethylpyridine / 1,2-dichloro-ethane / 72 h / 20 °C / Inert atmosphere

4.1: Thiobenzophenon; 2,4,6-tri-tert-butylpyrimidine / dichloromethane; toluene / 0.33 h / -60 °C / Molecular sieve

4.2: 2.16 h / -60 - 0 °C / Molecular sieve

With 2,6-dimethylpyridine; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; caesium carbonate; Thiobenzophenon; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.carres.2014.01.022