Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-isothiocyanatomethyl-2-(4-nitro-phenoxy)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-isothiocyanatomethyl-2-(4-nitro-phenoxy)-tetrahydro-pyran-3-yl ester
• CAS No.: 888323-08-8
• Molecular Formula: C₁₉H₂₀N₂O₁₀S
• Molecular Weight: 468.441

Synonyms:Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-isothiocyanatomethyl-2-(4-nitro-phenoxy)-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-isothiocyanatomethyl-2-(4-nitro-phenoxy)-tetrahydro-pyran-3-yl ester

Chemical Property:

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Technology Process of Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-isothiocyanatomethyl-2-(4-nitro-phenoxy)-tetrahydro-pyran-3-yl ester

There total 1 articles about Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-isothiocyanatomethyl-2-(4-nitro-phenoxy)-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:

Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-azidomethyl-2-(4-nitro-phenoxy)-tetrahydro-pyran-3-yl ester + carbon disulfide (75-15-0,12122-00-8) → Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-isothiocyanatomethyl-2-(4-nitro-phenoxy)-tetrahydro-pyran-3-yl ester (888323-08-8)

Guidance literature:

With triethyl phosphite;

DOI:10.1055/s-2006-926358

Reference yield: 100.0%

(3-methyl-3H-diazirin-3-yl)methanamine hydrochloride + Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-isothiocyanatomethyl-2-(4-nitro-phenoxy)-tetrahydro-pyran-3-yl ester (888323-08-8) → 4-nitrophenyl 2,3,4-tri-O-acetyl-6-(2'-azipropylthioureido)-6-deoxy-α-D-mannopyranoside

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1055/s-2006-926358

Reference yield:

Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-isothiocyanatomethyl-2-(4-nitro-phenoxy)-tetrahydro-pyran-3-yl ester (888323-08-8) → 4-nitrophenyl-6-deoxy-6-(2'-azipropylthioureido)-α-D-mannopyranoside

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / DIPEA / CH₂Cl₂ / 2 h / 20 °C

2: 91 percent / NaOMe / methanol / 0.5 h / 20 °C

With sodium methylate; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane;

DOI:10.1055/s-2006-926358

upstream raw materials:

carbon disulfide

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