Cbz-Ser(2-azido-2-deoxy-3,4-O-isopropylidene-α-D-galactopyranoside)-OMe

Base Information

• Chemical Name: Cbz-Ser(2-azido-2-deoxy-3,4-O-isopropylidene-α-D-galactopyranoside)-OMe
• CAS No.: 729602-74-8
• Molecular Formula: C₂₁H₂₈N₄O₉
• Molecular Weight: 480.475

Synonyms:Cbz-Ser(2-azido-2-deoxy-3,4-O-isopropylidene-α-D-galactopyranoside)-OMe

Chemical Property of Cbz-Ser(2-azido-2-deoxy-3,4-O-isopropylidene-α-D-galactopyranoside)-OMe

Chemical Property:

Purity/Quality:

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Technology Process of Cbz-Ser(2-azido-2-deoxy-3,4-O-isopropylidene-α-D-galactopyranoside)-OMe

There total 2 articles about Cbz-Ser(2-azido-2-deoxy-3,4-O-isopropylidene-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: 84.0%

2,2-dimethoxy-propane (77-76-9) + Cbz-Ser(2-azido-2-deoxy-α-D-galactopyranoside)-OMe (729602-72-6) → Cbz-Ser(2-azido-2-deoxy-3,4-O-isopropylidene-α-D-galactopyranoside)-OMe (729602-74-8)

Guidance literature:

With (R)-10-camphorsulfonic acid; In N,N-dimethyl-formamide; at 50 ℃; for 4h;

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-3,4-O-isopropylidene-α-D-galactopyranoside)-OMe (729602-74-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / Et₃N / methanol / 16 h

2: 84 percent / (1R)-(-)-camphorsulfonic acid / dimethylformamide / 4 h / 50 °C

With (R)-10-camphorsulfonic acid; triethylamine; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/ol0493195

Reference yield: 70.0%

Cbz-Ser(2-azido-2-deoxy-3,4-O-isopropylidene-α-D-galactopyranoside)-OMe (729602-74-8) + phenyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-3-O-acetyl-6-O-t-butyldiphenylsilyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-glucopyranoside (729602-75-9) → C62H78Cl3N5O25Si (729602-84-0)

Guidance literature:

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

DOI:10.1021/ol0493195

upstream raw materials:

2,2-dimethoxy-propane

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

Downstream raw materials:

C₆₂H₇₈Cl₃N₅O₂₅Si

3-{3-acetylamino-6-[3-acetylamino-4-hydroxy-6-hydroxymethyl-5-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxymethyl]-4,5-dihydroxy-tetrahydro-pyran-2-yloxy}-2-benzyloxycarbonylamino-propionic acid

2-benzyloxycarbonylamino-3-{4,5-diacetoxy-6-[4-acetoxy-3-acetylamino-6-hydroxymethyl-5-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxymethyl]-3-acetylamino-tetrahydro-pyran-2-yloxy}-propionic acid methyl ester

C₆₄H₈₃N₃O₂₇Si

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