4-O-allyl-2-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-gulcitol

Base Information

• Chemical Name: 4-O-allyl-2-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-gulcitol
• CAS No.: 161045-52-9
• Molecular Formula: C₂₄H₂₉NO₆
• Molecular Weight: 427.497

Synonyms:4-O-allyl-2-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-gulcitol

Chemical Property of 4-O-allyl-2-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-gulcitol

Chemical Property:

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Technology Process of 4-O-allyl-2-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-gulcitol

There total 16 articles about 4-O-allyl-2-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-gulcitol 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: 71.0%

methyl 3-O-allyl-5-O-benzyl-N-benzyloxycarbonyl-2,6-dideoxy-2,6-imino-α-L-gulofuranoside (161106-75-8) → 4-O-allyl-2-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-gulcitol (161045-52-9)

Guidance literature:

methyl 3-O-allyl-5-O-benzyl-N-benzyloxycarbonyl-2,6-dideoxy-2,6-imino-α-L-gulofuranoside; With trifluoroacetic acid; In 1,4-dioxane; water; at 20 ℃; for 11h;

With sodium tetrahydroborate; In ethanol; at 0 ℃; for 2h;

DOI:10.1016/S0040-4020(01)00642-1

Reference yield: 70.0%

methyl 3-O-allyl-5-O-benzyl-N-benzyloxycarbonyl-2,6-dideoxy-2,6-imino-β-L-gulofuranoside (372493-94-2) → 4-O-allyl-2-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-gulcitol (161045-52-9)

Guidance literature:

methyl 3-O-allyl-5-O-benzyl-N-benzyloxycarbonyl-2,6-dideoxy-2,6-imino-β-L-gulofuranoside; With trifluoroacetic acid; In 1,4-dioxane; water; at 20 ℃; for 11h;

With sodium tetrahydroborate; In ethanol; at 0 ℃; for 2h;

DOI:10.1016/S0040-4020(01)00642-1

Reference yield:

(1S,4S,5R,8R)-8-Allyloxy-4-benzyloxy-7-hydroxy-6-oxa-2-aza-bicyclo[3.2.1]octane-2-carboxylic acid benzyl ester → 4-O-allyl-2-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-gulcitol (161045-52-9)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 0 ℃; Yield given;

DOI:10.1246/cl.1994.2119

upstream raw materials:

methyl 3-O-allyl-5-O-benzyl-N-benzyloxycarbonyl-2,6-dideoxy-2,6-imino-β-L-gulofuranoside

methyl 3-O-allyl-5-O-benzyl-N-benzyloxycarbonyl-2,6-dideoxy-2,6-imino-α-L-gulofuranoside

(3aR,5R,6S,6aR)-6-(allyloxy)-5-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole

3-O-allyl-1,2-O-isopropylidene-α-D-glucofuranose

Downstream raw materials:

2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-glucitol

N-benzyloxycarbonyl-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-1,5-dideoxy-1,5-imino-D-gulcitol

4-O-allyl-N-benzyloxycarbonyl-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-1,5-dideoxy-1,5-imino-D-gulcitol

4-O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-α-D-glucopyranosyl)-N-benzyloxycarbonyl-2,3-di-O-benzyl-1,5-dideoxy-1,5-imino-D-gulcitol

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