Naphthalene-2-sulfonic acid (2S,3R,4S,5S,6R)-6-azidomethyl-2-benzyloxy-4,5-dihydroxy-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Naphthalene-2-sulfonic acid (2S,3R,4S,5S,6R)-6-azidomethyl-2-benzyloxy-4,5-dihydroxy-tetrahydro-pyran-3-yl ester
• CAS No.: 189878-83-9
• Molecular Formula: C₂₃H₂₃N₃O₇S
• Molecular Weight: 485.518

Synonyms:Naphthalene-2-sulfonic acid (2S,3R,4S,5S,6R)-6-azidomethyl-2-benzyloxy-4,5-dihydroxy-tetrahydro-pyran-3-yl ester

Chemical Property of Naphthalene-2-sulfonic acid (2S,3R,4S,5S,6R)-6-azidomethyl-2-benzyloxy-4,5-dihydroxy-tetrahydro-pyran-3-yl ester

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Technology Process of Naphthalene-2-sulfonic acid (2S,3R,4S,5S,6R)-6-azidomethyl-2-benzyloxy-4,5-dihydroxy-tetrahydro-pyran-3-yl ester

There total 2 articles about Naphthalene-2-sulfonic acid (2S,3R,4S,5S,6R)-6-azidomethyl-2-benzyloxy-4,5-dihydroxy-tetrahydro-pyran-3-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: 79.0%

C33H30O10S2 (189878-82-8) → Naphthalene-2-sulfonic acid (2S,3R,4S,5S,6R)-6-azidomethyl-2-benzyloxy-4,5-dihydroxy-tetrahydro-pyran-3-yl ester (189878-83-9)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 55 ℃; for 16h;

DOI:10.1002/anie.199707511

Reference yield:

benzyl α-D-glucopyranoside (25320-99-4) → Naphthalene-2-sulfonic acid (2S,3R,4S,5S,6R)-6-azidomethyl-2-benzyloxy-4,5-dihydroxy-tetrahydro-pyran-3-yl ester (189878-83-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) (Bu₃Sn)2O / 1.) PhMe, reflux, 4 h, 2.) 60 deg C, 15 h

2: 79 percent / NaN₃ / dimethylformamide / 16 h / 55 °C

With sodium azide; bis(tri-n-butyltin)oxide; In N,N-dimethyl-formamide;

DOI:10.1002/anie.199707511

Reference yield: 95.0%

Naphthalene-2-sulfonic acid (2S,3R,4S,5S,6R)-6-azidomethyl-2-benzyloxy-4,5-dihydroxy-tetrahydro-pyran-3-yl ester (189878-83-9) → Naphthalene-2-sulfonic acid (2S,3R,4S,5S,6R)-6-aminomethyl-2-benzyloxy-4,5-dihydroxy-tetrahydro-pyran-3-yl ester (189878-84-0)

Guidance literature:

With water; triphenylphosphine; In tetrahydrofuran; for 24h; Ambient temperature;

DOI:10.1002/anie.199707511

upstream raw materials:

C₃₃H₃₀O₁₀S₂

benzyl α-D-glucopyranoside

Downstream raw materials:

Naphthalene-2-sulfonic acid (2S,3R,4S,5S,6R)-6-aminomethyl-2-benzyloxy-4,5-dihydroxy-tetrahydro-pyran-3-yl ester

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