Acetic acid (2S,3R,4R,5S,6R)-3-acetylamino-5-hydroxy-6-[(3aR,4S,6R,7S,7aR)-7-(4-methoxy-benzyloxy)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxymethyl]-2-(4-nitro-phenoxy)-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3R,4R,5S,6R)-3-acetylamino-5-hydroxy-6-[(3aR,4S,6R,7S,7aR)-7-(4-methoxy-benzyloxy)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxymethyl]-2-(4-nitro-phenoxy)-tetrahydro-pyran-4-yl ester
• CAS No.: 130572-14-4
• Molecular Formula: C₃₃H₄₂N₂O₁₄
• Molecular Weight: 690.701

Synonyms:

Chemical Property of Acetic acid (2S,3R,4R,5S,6R)-3-acetylamino-5-hydroxy-6-[(3aR,4S,6R,7S,7aR)-7-(4-methoxy-benzyloxy)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxymethyl]-2-(4-nitro-phenoxy)-tetrahydro-pyran-4-yl ester

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Technology Process of Acetic acid (2S,3R,4R,5S,6R)-3-acetylamino-5-hydroxy-6-[(3aR,4S,6R,7S,7aR)-7-(4-methoxy-benzyloxy)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxymethyl]-2-(4-nitro-phenoxy)-tetrahydro-pyran-4-yl ester

There total 4 articles about Acetic acid (2S,3R,4R,5S,6R)-3-acetylamino-5-hydroxy-6-[(3aR,4S,6R,7S,7aR)-7-(4-methoxy-benzyloxy)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxymethyl]-2-(4-nitro-phenoxy)-tetrahydro-pyran-4-yl 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: 85.7%

4-nitrophenyl 2-acetamido-3-O-acetyl-2-deoxy-β-D-glucopyranoside (23262-57-9) + Methyl 3,4-O-Isopropylidene-2-O-(4-methoxybenzyl)-1-Thio-β-L-Fucopyranoside (130572-02-0) → Acetic acid (2S,3R,4R,5S,6R)-3-acetylamino-5-hydroxy-6-[(3aR,4S,6R,7S,7aR)-7-(4-methoxy-benzyloxy)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxymethyl]-2-(4-nitro-phenoxy)-tetrahydro-pyran-4-yl ester (130572-14-4)

Guidance literature:

With tetrabutylammomium bromide; copper(ll) bromide;

DOI:10.1016/S0040-4039(00)97612-3

Reference yield:

methyl 1-thio-β-L-fucopyranoside (114853-38-2) → Acetic acid (2S,3R,4R,5S,6R)-3-acetylamino-5-hydroxy-6-[(3aR,4S,6R,7S,7aR)-7-(4-methoxy-benzyloxy)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxymethyl]-2-(4-nitro-phenoxy)-tetrahydro-pyran-4-yl ester (130572-14-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 96.8 percent / p-toluenesulfonic acid / dimethylformamide

2: NaH, DMF

3: 85.7 percent / CuBr₂, Bu₄NBr

With tetrabutylammomium bromide; sodium hydride; toluene-4-sulfonic acid; N,N-dimethyl-formamide; copper(ll) bromide; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)97612-3

Reference yield:

methyl 3,4-O-isopropylidene-1-thio-β-L-fucopyranoside (130572-04-2) → Acetic acid (2S,3R,4R,5S,6R)-3-acetylamino-5-hydroxy-6-[(3aR,4S,6R,7S,7aR)-7-(4-methoxy-benzyloxy)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxymethyl]-2-(4-nitro-phenoxy)-tetrahydro-pyran-4-yl ester (130572-14-4)

Guidance literature:

Multi-step reaction with 2 steps

1: NaH, DMF

2: 85.7 percent / CuBr₂, Bu₄NBr

With tetrabutylammomium bromide; sodium hydride; N,N-dimethyl-formamide; copper(ll) bromide;

DOI:10.1016/S0040-4039(00)97612-3

upstream raw materials:

4-nitrophenyl 2-acetamido-3-O-acetyl-2-deoxy-β-D-glucopyranoside

Methyl 3,4-O-Isopropylidene-2-O-(4-methoxybenzyl)-1-Thio-β-L-Fucopyranoside

methyl 1-thio-β-L-fucopyranoside

methyl 3,4-O-isopropylidene-1-thio-β-L-fucopyranoside

Downstream raw materials:

p-nitrophenyl 2-acetamido-2-deoxy-6-O-α-L-fucopyranosyl-β-D-glucopyranoside

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