N-(tert-butoxycarbonyl)-S-[2-[(2-O-benzyl-4,6-O-benzylidene-3-O-(2-naphthylmethyl)-β-D-mannopyranosyloxy)methyl]allyl]-L-cysteine methyl ester

Base Information

Chemical Name:N-(tert-butoxycarbonyl)-S-[2-[(2-O-benzyl-4,6-O-benzylidene-3-O-(2-naphthylmethyl)-β-D-mannopyranosyloxy)methyl]allyl]-L-cysteine methyl ester
CAS No.:1407967-97-8
Molecular Formula:C₄₄H₅₁NO₁₀S
Molecular Weight:785.956
Hs Code.:

N-(tert-butoxycarbonyl)-S-[2-[(2-O-benzyl-4,6-O-benzylidene-3-O-(2-naphthylmethyl)-β-D-mannopyranosyloxy)methyl]allyl]-L-cysteine methyl ester

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Chemical Property of N-(tert-butoxycarbonyl)-S-[2-[(2-O-benzyl-4,6-O-benzylidene-3-O-(2-naphthylmethyl)-β-D-mannopyranosyloxy)methyl]allyl]-L-cysteine methyl ester

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Technology Process of N-(tert-butoxycarbonyl)-S-[2-[(2-O-benzyl-4,6-O-benzylidene-3-O-(2-naphthylmethyl)-β-D-mannopyranosyloxy)methyl]allyl]-L-cysteine methyl ester

There total 5 articles about N-(tert-butoxycarbonyl)-S-[2-[(2-O-benzyl-4,6-O-benzylidene-3-O-(2-naphthylmethyl)-β-D-mannopyranosyloxy)methyl]allyl]-L-cysteine methyl ester 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: 57.0%

: 1407967-82-1
2-(selenocyanatomethyl)allyl 2-O-benzyl-4,6-O-benzylidene-3-O-(2-naphthylmethyl)-β-D-mannopyranoside

: 172749-96-1
N-[(tert-butoxy)carbonyl]-L-cysteine methyl ester

: 1407967-97-8
N-(tert-butoxycarbonyl)-S-[2-[(2-O-benzyl-4,6-O-benzylidene-3-O-(2-naphthylmethyl)-β-D-mannopyranosyloxy)methyl]allyl]-L-cysteine methyl ester

Guidance literature:: In methanol; at 20 ℃; Inert atmosphere;
DOI:10.1139/v2012-056

Reference yield:

: 100-39-0
benzyl bromide

: 1407967-97-8
N-(tert-butoxycarbonyl)-S-[2-[(2-O-benzyl-4,6-O-benzylidene-3-O-(2-naphthylmethyl)-β-D-mannopyranosyloxy)methyl]allyl]-L-cysteine methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: di(n-butyl)tin oxide / toluene / Inert atmosphere; Reflux

1.2: 6 h / 20 °C / Inert atmosphere

1.3: 0 - 20 °C / Inert atmosphere

2.1: 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpyrimidine / dichloromethane / 1 h / -78 °C / Inert atmosphere

2.2: 1 h / -78 °C / Inert atmosphere

3.1: methanol / 20 °C / Inert atmosphere

With 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; di(n-butyl)tin oxide; 2,4,6-tri-tert-butylpyrimidine; In methanol; dichloromethane; toluene;
DOI:10.1139/v2012-056

Reference yield:

: 1407967-81-0
(4-methylphenyl) 2-O-benzyl-4,6-O-benzylidene-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside

: 1407967-97-8
N-(tert-butoxycarbonyl)-S-[2-[(2-O-benzyl-4,6-O-benzylidene-3-O-(2-naphthylmethyl)-β-D-mannopyranosyloxy)methyl]allyl]-L-cysteine methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpyrimidine / dichloromethane / 1 h / -78 °C / Inert atmosphere

1.2: 1 h / -78 °C / Inert atmosphere

2.1: methanol / 20 °C / Inert atmosphere

With 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpyrimidine; In methanol; dichloromethane;
DOI:10.1139/v2012-056