Cbz-Ser(2-azido-2-deoxy-6-tert-butyldimethylsilyl-α-D-galactopyranoside)-OMe

Base Information

• Chemical Name: Cbz-Ser(2-azido-2-deoxy-6-tert-butyldimethylsilyl-α-D-galactopyranoside)-OMe
• CAS No.: 729602-73-7
• Molecular Formula: C₂₄H₃₈N₄O₉Si
• Molecular Weight: 554.673

Synonyms:Cbz-Ser(2-azido-2-deoxy-6-tert-butyldimethylsilyl-α-D-galactopyranoside)-OMe

Chemical Property of Cbz-Ser(2-azido-2-deoxy-6-tert-butyldimethylsilyl-α-D-galactopyranoside)-OMe

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Technology Process of Cbz-Ser(2-azido-2-deoxy-6-tert-butyldimethylsilyl-α-D-galactopyranoside)-OMe

There total 2 articles about Cbz-Ser(2-azido-2-deoxy-6-tert-butyldimethylsilyl-α-D-galactopyranoside)-OMe 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: 92.0%

tert-butyldimethylsilyl chloride (18162-48-6) + Cbz-Ser(2-azido-2-deoxy-α-D-galactopyranoside)-OMe (729602-72-6) → Cbz-Ser(2-azido-2-deoxy-6-tert-butyldimethylsilyl-α-D-galactopyranoside)-OMe (729602-73-7)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 16h;

DOI:10.1021/ol0493195

Reference yield:

3-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-serine methyl ester (74084-36-9) → Cbz-Ser(2-azido-2-deoxy-6-tert-butyldimethylsilyl-α-D-galactopyranoside)-OMe (729602-73-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / Et₃N / methanol / 16 h

2: 92 percent / imidazole / dimethylformamide / 16 h

With 1H-imidazole; triethylamine; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/ol0493195

Reference yield: 73.0%

Acetic acid (2R,4aR,6S,7R,8S,8aS)-7-acetoxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester + Cbz-Ser(2-azido-2-deoxy-6-tert-butyldimethylsilyl-α-D-galactopyranoside)-OMe (729602-73-7) → 3-[3-azido-6-(tert-butyl-dimethyl-silanyloxymethyl)-4-(7,8-diacetoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-5-hydroxy-tetrahydro-pyran-2-yloxy]-2-benzyloxycarbonylamino-propionic acid methyl ester

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1021/ol0493195

upstream raw materials:

tert-butyldimethylsilyl chloride

Cbz-Ser(2-azido-2-deoxy-α-D-galactopyranoside)-OMe

3-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-serine methyl ester

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