cyclohexyl 3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-α-D-glucopyranoside

Base Information

• Chemical Name: cyclohexyl 3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-α-D-glucopyranoside
• CAS No.: 21559-74-0
• Molecular Formula: C₂₀H₃₁NO₉
• Molecular Weight: 429.467

Synonyms:cyclohexyl 3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-α-D-glucopyranoside

Chemical Property of cyclohexyl 3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-α-D-glucopyranoside

Chemical Property:

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Technology Process of cyclohexyl 3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-α-D-glucopyranoside

There total 8 articles about cyclohexyl 3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-α-D-glucopyranoside 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: 66.0%

cyclohexanol (108-93-0) + Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester (3068-34-6) → cyclohexyl 3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranoside (21588-60-3) + cyclohexyl 3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-α-D-glucopyranoside (21559-74-0)

Guidance literature:

With 3 A molecular sieve; mercury(II) iodide; In 1,2-dichloro-ethane; at 90 - 95 ℃; for 2h; Yields of byproduct given;

Reference yield: 63.6%

2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl diphenylphosphinate (297132-68-4) + cyclohexanol (108-93-0) → cyclohexyl 3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranoside (21588-60-3) + cyclohexyl 3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-α-D-glucopyranoside (21559-74-0)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In nitromethane; for 2h; Heating;

DOI:10.1016/S0008-6215(00)00069-0

Reference yield: 48.0%

cyclohexanol (108-93-0) + Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester (3068-34-6) → cyclohexyl 3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-α-D-glucopyranoside (21559-74-0)

Guidance literature:

With 3 A molecular sieve; mercury(II) iodide; In nitromethane; Heating;

upstream raw materials:

acetic anhydride

cyclohexanol

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester

2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl diphenylphosphinate

Downstream raw materials:

cyclohexyl 2-(acetylamino)-2-deoxy-α-D-glucopyranoside

cyclohexyl 2-(acetylamino)-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside

cyclohexyl 2-(acetylamino)-2-deoxy-4,6-O-isopropylidene-3-O-[(R)-1-carboxyethyl]-α-D-glucopyranoside

(R)-4-{(S)-2-[(R)-2-((2S,3R,4R,5S,6R)-3-Acetylamino-2-cyclohexyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy)-propionylamino]-propionylamino}-4-carbamoyl-butyric acid benzyl ester

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