methyl 6-{[(benzyloxy)carbonyl]amino}-1-{3-[(benzyloxy)methyl]uracil-1-yl}-6-deoxy-2,3-O-isopropylidene-β-D-glycero-L-talo-heptofuranuronate

Base Information

• Chemical Name: methyl 6-{[(benzyloxy)carbonyl]amino}-1-{3-[(benzyloxy)methyl]uracil-1-yl}-6-deoxy-2,3-O-isopropylidene-β-D-glycero-L-talo-heptofuranuronate
• CAS No.: 852068-15-6
• Molecular Formula: C₃₁H₃₅N₃O₁₁
• Molecular Weight: 625.632

Synonyms:methyl 6-{[(benzyloxy)carbonyl]amino}-1-{3-[(benzyloxy)methyl]uracil-1-yl}-6-deoxy-2,3-O-isopropylidene-β-D-glycero-L-talo-heptofuranuronate

Chemical Property of methyl 6-{[(benzyloxy)carbonyl]amino}-1-{3-[(benzyloxy)methyl]uracil-1-yl}-6-deoxy-2,3-O-isopropylidene-β-D-glycero-L-talo-heptofuranuronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 6-{[(benzyloxy)carbonyl]amino}-1-{3-[(benzyloxy)methyl]uracil-1-yl}-6-deoxy-2,3-O-isopropylidene-β-D-glycero-L-talo-heptofuranuronate

There total 6 articles about methyl 6-{[(benzyloxy)carbonyl]amino}-1-{3-[(benzyloxy)methyl]uracil-1-yl}-6-deoxy-2,3-O-isopropylidene-β-D-glycero-L-talo-heptofuranuronate 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: 61.0%

(E)-3-[(3aR,4R,6R,6aR)-6-(3-Benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-acrylic acid methyl ester (852068-14-5) + O-benzyl carbamate (621-84-1) → methyl 6-{[(benzyloxy)carbonyl]amino}-1-{3-[(benzyloxy)methyl]uracil-1-yl}-6-deoxy-2,3-O-isopropylidene-β-D-glycero-L-talo-heptofuranuronate (852068-15-6)

Guidance literature:

With sodium hydroxide; potassium dioxotetrahydroxoosmate(VI); hydroquinidine anthraquinone-1,4-diyl diether; tert-butylhypochlorite; In propan-1-ol; water;

DOI:10.1081/NCN-200059769

Reference yield: 52.0%

(E)-3-[(3aR,4R,6R,6aR)-6-(3-Benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-acrylic acid methyl ester (852068-14-5) + O-benzyl carbamate (621-84-1) → methyl 6-{[(benzyloxy)carbonyl]amino}-1-{3-[(benzyloxy)methyl]uracil-1-yl}-6-deoxy-2,3-O-isopropylidene-α-L-glycero-D-allo-heptofuranuronate (852068-27-0) + methyl 6-{[(benzyloxy)carbonyl]amino}-1-{3-[(benzyloxy)methyl]uracil-1-yl}-6-deoxy-2,3-O-isopropylidene-β-D-glycero-L-talo-heptofuranuronate (852068-15-6)

Guidance literature:

O-benzyl carbamate; With sodium hydroxide; tert-butylhypochlorite; In propan-1-ol; water; at 15 - 20 ℃;

(E)-3-[(3aR,4R,6R,6aR)-6-(3-Benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-acrylic acid methyl ester; With 1,4-bis(dihydroquinidinyl)anthraquinone; K2; In propan-1-ol; water; at 20 ℃; for 2h;

DOI:10.1002/anie.200462439

Reference yield: 52.0%

methyl 1-(3-benzyloxymethyluracil-1-yl)-5,6-dideoxy-2,3-O-isopropylidene-β-D-ribo-hept-5-enofuranouronate + O-benzyl carbamate (621-84-1) → methyl 6-{[(benzyloxy)carbonyl]amino}-1-{3-[(benzyloxy)methyl]uracil-1-yl}-6-deoxy-2,3-O-isopropylidene-α-L-glycero-D-allo-heptofuranuronate (852068-27-0) + methyl 6-{[(benzyloxy)carbonyl]amino}-1-{3-[(benzyloxy)methyl]uracil-1-yl}-6-deoxy-2,3-O-isopropylidene-β-D-glycero-L-talo-heptofuranuronate (852068-15-6)

Guidance literature:

With sodium hydroxide; tert-butylhypochlorite; potassium dioxotetrahydroxoosmate(VI); In propan-1-ol; water; at 20 ℃; for 2h;

DOI:10.1021/jo701699h

upstream raw materials:

(E)-3-[(3aR,4R,6R,6aR)-6-(3-Benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-acrylic acid methyl ester

O-benzyl carbamate

2',3'-O-isopropylideneuridine

(methyl 5',6'-dideoxy-2',3'-isopropylidene-6'-β-D-ribo-5'-ene-hexofuranuronate)-1-uracil

Downstream raw materials:

methyl 5-O-[5-azido-5-deoxy-2,3-O-(3-pentylidene)-β-D-ribofuranosyl]-6-{[(benzyloxy)carbonyl]amino}-1-{3-[(benzyloxy)methyl]uracil-1-yl}-6-deoxy-2,3-O-isopropylidene-β-D-glycero-L-talo-heptofuranuronate

methyl 5-O-(5-azido-5-deoxy-2,3-O-isopropylidene-β-D-ribofuranosyl)-6-benzyloxycarbonylamino-1-(3-benzyloxymethyluracil-1-yl)-6-deoxy-2,3-O-isopropylidene-β-D-glycero-L-talo-heptofuranuronate

methyl 5-O-(5-azido-5-deoxy-2,3-O-isopropylidene-α-D-ribofuranosyl)-6-benzyloxycarbonylamino-1-(3-benzyloxymethyluracil-1-yl)-6-deoxy-2,3-O-isopropylidene-β-D-glycero-L-talo-heptofuranuronate

methyl 5-O-(5-azido-5-deoxy-2,3-O-cyclopentylidene-β-D-ribofuranosyl)-6-benzyloxycarbonylamino-1-(3-benzyloxymethyluracil-1-yl)-6-deoxy-2,3-O-isopropylidene-β-D-glycero-L-talo-heptofuranuronate

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