benzyl ((2S,3R,4R,5S,6R)-2-(allyloxy)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)carbamate

Base Information

• Chemical Name: benzyl ((2S,3R,4R,5S,6R)-2-(allyloxy)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)carbamate
• CAS No.: 83663-03-0
• Molecular Formula: C₁₇H₂₃NO₇
• Molecular Weight: 353.372

Synonyms:benzyl ((2S,3R,4R,5S,6R)-2-(allyloxy)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)carbamate

Chemical Property of benzyl ((2S,3R,4R,5S,6R)-2-(allyloxy)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)carbamate

Chemical Property:

Purity/Quality:

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Technology Process of benzyl ((2S,3R,4R,5S,6R)-2-(allyloxy)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)carbamate

There total 4 articles about benzyl ((2S,3R,4R,5S,6R)-2-(allyloxy)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)carbamate 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: 55.0%

2-carbobenzyloxyamino-2-deoxy-D-glucopyranose (3006-58-4,13030-01-8,42890-10-8,42973-23-9,77059-32-6,121785-09-9,7474-40-0) + allyl alcohol (107-18-6) → benzyl ((2S,3R,4R,5S,6R)-2-(allyloxy)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)carbamate (83663-03-0) + allyl 2-benzyloxycarbonylamino-2-deoxy-β-D-glucopyranoside

Guidance literature:

With acetyl chloride; for 43h; Heating;

DOI:10.1016/S0008-6215(99)00190-1

Reference yield: 52.0%

2-carbobenzyloxyamino-2-deoxy-D-glucopyranose (3006-58-4,13030-01-8,42890-10-8,42973-23-9,77059-32-6,121785-09-9,7474-40-0) + allyl alcohol (107-18-6) → benzyl ((2S,3R,4R,5S,6R)-2-(allyloxy)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)carbamate (83663-03-0)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 60 ℃; for 4h;

DOI:10.1039/c5ob00211g

Reference yield:

benzyl ((2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)carbamate (77059-32-6) + allyl alcohol (107-18-6) → benzyl ((2S,3R,4R,5S,6R)-2-(allyloxy)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)carbamate (83663-03-0)

Guidance literature:

With hydrogenchloride; at 100 ℃; for 0.5h;

DOI:10.1016/S0040-4039(00)87506-1

upstream raw materials:

benzyl ((2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)carbamate

allyl alcohol

2-carbobenzyloxyamino-2-deoxy-D-glucopyranose

(+)-D-glucosamine hydrochloride

Downstream raw materials:

C₃₁H₃₁NO₉

C₃₂H₃₃NO₁₁S

propyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-α-D-glucopyranoside

((1R,2R,4S,5R,6R)-4-Allyloxy-2-hydroxymethyl-3,7-dioxa-bicyclo[4.1.0]hept-5-yl)-carbamic acid benzyl ester

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