N-[2-(2-O-acetyl-3-O-allyl-6-O-tert-butyldiphenylsilyl-β-D-glucopyranosylsulfanyl)ethyl]succinimide

Base Information

• Chemical Name: N-[2-(2-O-acetyl-3-O-allyl-6-O-tert-butyldiphenylsilyl-β-D-glucopyranosylsulfanyl)ethyl]succinimide
• CAS No.: 217642-64-3
• Molecular Formula: C₃₃H₄₃NO₈SSi
• Molecular Weight: 641.858
• Mol file: 217642-64-3.mol

Synonyms:N-[2-(2-O-acetyl-3-O-allyl-6-O-tert-butyldiphenylsilyl-β-D-glucopyranosylsulfanyl)ethyl]succinimide

Chemical Property of N-[2-(2-O-acetyl-3-O-allyl-6-O-tert-butyldiphenylsilyl-β-D-glucopyranosylsulfanyl)ethyl]succinimide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[2-(2-O-acetyl-3-O-allyl-6-O-tert-butyldiphenylsilyl-β-D-glucopyranosylsulfanyl)ethyl]succinimide

There total 5 articles about N-[2-(2-O-acetyl-3-O-allyl-6-O-tert-butyldiphenylsilyl-β-D-glucopyranosylsulfanyl)ethyl]succinimide 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: 90.0%

tert-butylchlorodiphenylsilane (58479-61-1) + N-[2-(2-O-acetyl-3-O-allyl-β-D-glucopyranosylsulfanyl)ethyl]succinimide (217642-63-2) → N-[2-(2-O-acetyl-3-O-allyl-6-O-tert-butyldiphenylsilyl-β-D-glucopyranosylsulfanyl)ethyl]succinimide (217642-64-3)

Guidance literature:

With dmap; In dichloromethane;

DOI:10.1002/(SICI)1521-3773(19981002)37:18<2503::AID-ANIE2503>3.0.CO;2-R

Reference yield:

Succinic acid methyl ester monocysteamide (163924-98-9) → N-[2-(2-O-acetyl-3-O-allyl-6-O-tert-butyldiphenylsilyl-β-D-glucopyranosylsulfanyl)ethyl]succinimide (217642-64-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / BF₃*OEt₂ / CH₂Cl₂ / 6 h / 0 - 25 °C

2: 90 percent / NaOMe / methanol / 6 h / 0 °C

3: 90 percent / imidazole; DMAP / CH₂Cl₂ / 2 h / 20 °C

With 1H-imidazole; dmap; boron trifluoride diethyl etherate; sodium methylate; In methanol; dichloromethane;

DOI:10.1016/S0008-6215(02)00301-4

Reference yield:

methyl N-[2-(2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranosylsulfanyl)ethyl]succinamate (217642-62-1) → N-[2-(2-O-acetyl-3-O-allyl-6-O-tert-butyldiphenylsilyl-β-D-glucopyranosylsulfanyl)ethyl]succinimide (217642-64-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / NaOMe / methanol / 6 h / 0 °C

2: 90 percent / imidazole; DMAP / CH₂Cl₂ / 2 h / 20 °C

With 1H-imidazole; dmap; sodium methylate; In methanol; dichloromethane;

DOI:10.1016/S0008-6215(02)00301-4

upstream raw materials:

tert-butylchlorodiphenylsilane

N-[2-(2-O-acetyl-3-O-allyl-β-D-glucopyranosylsulfanyl)ethyl]succinimide

Succinic acid methyl ester monocysteamide

methyl N-[2-(2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranosylsulfanyl)ethyl]succinamate

Downstream raw materials:

N-{2-[4-allyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-(1-ethoxy-ethoxy)-3-hydroxy-tetrahydro-pyran-2-ylsulfanyl]-ethyl}-N'-benzyl-succinamide

N-{2-[(2S,3R,4S,5R,6R)-3-Acetoxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-(1-ethoxy-ethoxy)-4-propoxy-tetrahydro-pyran-2-ylsulfanyl]-ethyl}-succinamic acid

N-{2-[(2S,3R,4S,5R,6R)-3-Acetoxy-4-allyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-(1-ethoxy-ethoxy)-tetrahydro-pyran-2-ylsulfanyl]-ethyl}-succinamic acid

Acetic acid (2S,3R,4S,5R,6R)-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-[2-(2,5-dioxo-pyrrolidin-1-yl)-ethylsulfanyl]-5-(1-ethoxy-ethoxy)-4-propoxy-tetrahydro-pyran-3-yl ester