benzyl 2-(benzyloxycarbonylamino)-2-deoxy-3-O--β-D-glucofuranoside

Base Information

• Chemical Name: benzyl 2-(benzyloxycarbonylamino)-2-deoxy-3-O--β-D-glucofuranoside
• CAS No.: 81148-68-7
• Molecular Formula: C₂₅H₃₁NO₉
• Molecular Weight: 489.522

Synonyms:benzyl 2-(benzyloxycarbonylamino)-2-deoxy-3-O--β-D-glucofuranoside

Chemical Property of benzyl 2-(benzyloxycarbonylamino)-2-deoxy-3-O--β-D-glucofuranoside

Chemical Property:

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Technology Process of benzyl 2-(benzyloxycarbonylamino)-2-deoxy-3-O--β-D-glucofuranoside

There total 2 articles about benzyl 2-(benzyloxycarbonylamino)-2-deoxy-3-O--β-D-glucofuranoside 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: 86.0%

benzyl 2-(benzyloxycarbonylamino)-2-deoxy-5,6-O-isopropylidene-3-O--β-D-glucofuranoside (80134-60-7) → benzyl 2-(benzyloxycarbonylamino)-2-deoxy-3-O--β-D-glucofuranoside (81148-68-7)

Guidance literature:

With acetic acid; In water; at 45 ℃; for 2h; Heating;

DOI:10.1016/S0008-6215(00)80687-4

Reference yield:

benzyl 2-(benzyloxycarbonyl)amino-3-O-(D-1-carboxyethyl)-2-deoxy-5,6-O-isopropylidene-β-D-glucofuranoside (74072-31-4) → benzyl 2-(benzyloxycarbonylamino)-2-deoxy-3-O--β-D-glucofuranoside (81148-68-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / diethyl ether / 1 h / Ambient temperature

2: 86 percent / 60 percent acetic acid / H₂O / 2 h / 45 °C / Heating

With acetic acid; In diethyl ether; water;

DOI:10.1016/S0008-6215(00)80687-4

Reference yield: 89.0%

methanesulfonyl chloride (124-63-0) + benzyl 2-(benzyloxycarbonylamino)-2-deoxy-3-O--β-D-glucofuranoside (81148-68-7) → benzyl 2-(benzyloxycarbonylamino)-2-deoxy-6-O-mesyl-3-O--β-D-glucofuranoside (81148-76-7)

Guidance literature:

With pyridine; at -10 ℃; for 5h;

DOI:10.1016/S0008-6215(00)80687-4

upstream raw materials:

benzyl 2-(benzyloxycarbonylamino)-2-deoxy-5,6-O-isopropylidene-3-O--β-D-glucofuranoside

benzyl 2-(benzyloxycarbonyl)amino-3-O-(D-1-carboxyethyl)-2-deoxy-5,6-O-isopropylidene-β-D-glucofuranoside

Downstream raw materials:

benzyl 2-(benzyloxycarbonylamino)-2-deoxy-6-O-mesyl-3-O--β-D-glucofuranoside

(R)-2-{(2R,3R,4R,5R)-4-Amino-5-benzyloxy-2-[(R)-2-octanoylamino-1-(tetrahydro-pyran-2-yloxy)-ethyl]-tetrahydro-furan-3-yloxy}-propionic acid methyl ester

(R)-2-{(2R,3R,4R,5R)-2-[(R)-2-Amino-1-(tetrahydro-pyran-2-yloxy)-ethyl]-5-benzyloxy-4-benzyloxycarbonylamino-tetrahydro-furan-3-yloxy}-propionic acid methyl ester

(R)-2-{(2R,3R,4R,5R)-4-Amino-5-benzyloxy-2-[(R)-2-hexadecanoylamino-1-(tetrahydro-pyran-2-yloxy)-ethyl]-tetrahydro-furan-3-yloxy}-propionic acid methyl ester

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