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

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Chemical Name:methyl 6-{[(benzyloxy)carbonyl]amino}-1-{3-[(benzyloxy)methyl]uracil-1-yl}-6-deoxy-2,3-O-isopropylidene-α-L-glycero-D-allo-heptofuranuronate
CAS No.:852068-27-0
Molecular Formula:C₃₁H₃₅N₃O₁₁
Molecular Weight:625.632
Hs Code.:

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

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

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

There total 5 articles about methyl 6-{[(benzyloxy)carbonyl]amino}-1-{3-[(benzyloxy)methyl]uracil-1-yl}-6-deoxy-2,3-O-isopropylidene-α-L-glycero-D-allo-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: 52.0%

: 852068-14-5
(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

: 621-84-1
O-benzyl carbamate

: 852068-27-0
methyl 6-{[(benzyloxy)carbonyl]amino}-1-{3-[(benzyloxy)methyl]uracil-1-yl}-6-deoxy-2,3-O-isopropylidene-α-L-glycero-D-allo-heptofuranuronate

: 852068-15-6
methyl 6-{[(benzyloxy)carbonyl]amino}-1-{3-[(benzyloxy)methyl]uracil-1-yl}-6-deoxy-2,3-O-isopropylidene-β-D-glycero-L-talo-heptofuranuronate

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

: 621-84-1
O-benzyl carbamate

: 852068-27-0
methyl 6-{[(benzyloxy)carbonyl]amino}-1-{3-[(benzyloxy)methyl]uracil-1-yl}-6-deoxy-2,3-O-isopropylidene-α-L-glycero-D-allo-heptofuranuronate

: 852068-15-6
methyl 6-{[(benzyloxy)carbonyl]amino}-1-{3-[(benzyloxy)methyl]uracil-1-yl}-6-deoxy-2,3-O-isopropylidene-β-D-glycero-L-talo-heptofuranuronate

Guidance literature:: With sodium hydroxide; tert-butylhypochlorite; potassium dioxotetrahydroxoosmate(VI); In propan-1-ol; water; at 20 ℃; for 2h;
DOI:10.1021/jo701699h

Reference yield:

: 362-43-6
2',3'-O-isopropylideneuridine

: 852068-27-0
methyl 6-{[(benzyloxy)carbonyl]amino}-1-{3-[(benzyloxy)methyl]uracil-1-yl}-6-deoxy-2,3-O-isopropylidene-α-L-glycero-D-allo-heptofuranuronate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 1-hydroxy-1,2-benziodoxol-3-(1H)-one 1-oxide / acetonitrile / 1 h / 80 °C

2.1: CH₂Cl₂ / 1 h / -20 °C

3.1: 12.4 g / Bu₄NI; Na₂CO₃ / CH₂Cl₂; H₂O / 12 h / 20 °C

4.1: t-butyl hypochlorite; NaOH / H₂O; propan-1-ol / 15 - 20 °C

4.2: 8.5 percent / 1,4-bis(dihydroquinidinyl)anthraquinone; K₂[OsO₂(OH)4] / propan-1-ol; H₂O / 2 h / 20 °C

With sodium hydroxide; tert-butylhypochlorite; tetra-(n-butyl)ammonium iodide; sodium carbonate; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In propan-1-ol; dichloromethane; water; acetonitrile; 4.2: Sharpless aminohydroxylation;
DOI:10.1002/anie.200462439