N-benzyloxycarbonyl-O-[O-(2-O-acetyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->4)-(3-O-acetyl-2-O-dibenzyloxyphosphinyl-β-D-xylopyranosyl)]-L-serine benzyl ester

Base Information

• Chemical Name: N-benzyloxycarbonyl-O-[O-(2-O-acetyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->4)-(3-O-acetyl-2-O-dibenzyloxyphosphinyl-β-D-xylopyranosyl)]-L-serine benzyl ester
• CAS No.: 343254-36-4
• Molecular Formula: C₅₄H₅₈NO₁₉P
• Molecular Weight: 1056.02
• Mol file: 343254-36-4.mol

Synonyms:N-benzyloxycarbonyl-O-[O-(2-O-acetyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->4)-(3-O-acetyl-2-O-dibenzyloxyphosphinyl-β-D-xylopyranosyl)]-L-serine benzyl ester

Chemical Property of N-benzyloxycarbonyl-O-[O-(2-O-acetyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->4)-(3-O-acetyl-2-O-dibenzyloxyphosphinyl-β-D-xylopyranosyl)]-L-serine benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-benzyloxycarbonyl-O-[O-(2-O-acetyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->4)-(3-O-acetyl-2-O-dibenzyloxyphosphinyl-β-D-xylopyranosyl)]-L-serine benzyl ester

There total 12 articles about N-benzyloxycarbonyl-O-[O-(2-O-acetyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->4)-(3-O-acetyl-2-O-dibenzyloxyphosphinyl-β-D-xylopyranosyl)]-L-serine benzyl 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: 95.0%

N-benzyloxycarbonyl-O-{O-(2-O-acetyl-3-O-allyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->4)-(3-O-acetyl-2-O-dibenzyloxyphosphinyl-β-D-xylopyranosyl)}-L-serine benzyl ester (343254-49-9) → N-benzyloxycarbonyl-O-[O-(2-O-acetyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->4)-(3-O-acetyl-2-O-dibenzyloxyphosphinyl-β-D-xylopyranosyl)]-L-serine benzyl ester (343254-36-4)

Guidance literature:

N-benzyloxycarbonyl-O-{O-(2-O-acetyl-3-O-allyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->4)-(3-O-acetyl-2-O-dibenzyloxyphosphinyl-β-D-xylopyranosyl)}-L-serine benzyl ester; With hydrogen; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; In tetrahydrofuran; for 2h;

With iodine; sodium hydrogencarbonate; In tetrahydrofuran; water; for 0.25h; Further stages.;

DOI:10.1021/jo001540h

Reference yield:

D-Xylose (87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,36562-42-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2) → N-benzyloxycarbonyl-O-[O-(2-O-acetyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->4)-(3-O-acetyl-2-O-dibenzyloxyphosphinyl-β-D-xylopyranosyl)]-L-serine benzyl ester (343254-36-4)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 86 percent / pyridine; DMAP / 1,2-dichloro-ethane / 20 °C

2.1: 29 percent / TMSOTf / CH₂Cl₂ / 6 h / -20 °C

3.1: NH₂NH₂*AcOH / toluene; ethanol / 0.67 h

4.1: Bu₂SnO / dioxane / 1.5 h / Heating

4.2: 62 percent / CH₂Cl₂ / 1.33 h

5.1: 78 percent / pyridine; CH₂Cl₂ / 0.67 h / 0 °C

6.1: 88 percent / 1H-tetrazole / CH₂Cl₂ / 0.83 h / 20 °C

7.1: 88 percent / hydrazine acetate / ethanol; toluene / 1.5 h

8.1: 37 percent / MS AW₃₀₀; NIS; TfOH / 1,2-dichloro-ethane; diethyl ether / 0.5 h / -20 °C

9.1: H₂ / Ir(COD)(PMePh₂)PF₆ / tetrahydrofuran / 2 h

9.2: 95 percent / I₂; NaHCO₃ / tetrahydrofuran; H₂O / 0.25 h

With pyridine; 1H-tetrazole; dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; MS AW₃₀₀; hydrogen; hydrazinium monoacetate; di(n-butyl)tin oxide; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; In tetrahydrofuran; 1,4-dioxane; pyridine; diethyl ether; ethanol; dichloromethane; 1,2-dichloro-ethane; toluene;

DOI:10.1021/jo001540h

Reference yield:

1,2,3,4-tetra-O-levulinoyl-α-D-xylopyranose (343254-30-8) → N-benzyloxycarbonyl-O-[O-(2-O-acetyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->4)-(3-O-acetyl-2-O-dibenzyloxyphosphinyl-β-D-xylopyranosyl)]-L-serine benzyl ester (343254-36-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 29 percent / TMSOTf / CH₂Cl₂ / 6 h / -20 °C

2.1: NH₂NH₂*AcOH / toluene; ethanol / 0.67 h

3.1: Bu₂SnO / dioxane / 1.5 h / Heating

3.2: 62 percent / CH₂Cl₂ / 1.33 h

4.1: 78 percent / pyridine; CH₂Cl₂ / 0.67 h / 0 °C

5.1: 88 percent / 1H-tetrazole / CH₂Cl₂ / 0.83 h / 20 °C

6.1: 88 percent / hydrazine acetate / ethanol; toluene / 1.5 h

7.1: 37 percent / MS AW₃₀₀; NIS; TfOH / 1,2-dichloro-ethane; diethyl ether / 0.5 h / -20 °C

8.1: H₂ / Ir(COD)(PMePh₂)PF₆ / tetrahydrofuran / 2 h

8.2: 95 percent / I₂; NaHCO₃ / tetrahydrofuran; H₂O / 0.25 h

With 1H-tetrazole; N-iodo-succinimide; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; MS AW₃₀₀; hydrogen; hydrazinium monoacetate; di(n-butyl)tin oxide; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; In tetrahydrofuran; 1,4-dioxane; pyridine; diethyl ether; ethanol; dichloromethane; 1,2-dichloro-ethane; toluene;

DOI:10.1021/jo001540h

upstream raw materials:

N-benzyloxycarbonyl-O-{O-(2-O-acetyl-3-O-allyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->4)-(3-O-acetyl-2-O-dibenzyloxyphosphinyl-β-D-xylopyranosyl)}-L-serine benzyl ester

D-Xylose

Dibenzyl N,N-diisopropylphosphoramidite

methyl 2-O-acetyl-3-O-allyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside