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

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Chemical Name: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
CAS No.:852068-17-8
Molecular Formula:C₄₁H₅₀N₆O₁₄
Molecular Weight:850.88
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 5 articles about 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 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: 77.0%

: 5-azido-5-deoxy-2,3-O-(3-pentylidene)-D-ribofuranosyl fluoride

: 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

: 852068-17-8
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-(3-pentylidene)-α-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

Guidance literature:: With 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; at -30 ℃;
DOI:10.1002/anie.200462439

Reference yield:

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

: 852068-17-8
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

Guidance literature:: Multi-step reaction with 5 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: 52 percent / 1,4-bis(dihydroquinidinyl)anthraquinone; K₂[OsO₂(OH)4] / propan-1-ol; H₂O / 2 h / 20 °C

5.1: 77 percent / molecular sieves 4 Angstroem; BF₃*Et₂O / CH₂Cl₂ / -30 °C

With sodium hydroxide; tert-butylhypochlorite; 4 A molecular sieve; boron trifluoride diethyl etherate; 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

Reference yield:

: 27999-65-1
(3aS,4S,6R,6aR)-6-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbaldehyde

: 852068-17-8
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

Guidance literature:: Multi-step reaction with 4 steps

1.1: CH₂Cl₂ / 1 h / -20 °C

2.1: 12.4 g / Bu₄NI; Na₂CO₃ / CH₂Cl₂; H₂O / 12 h / 20 °C

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

3.2: 52 percent / 1,4-bis(dihydroquinidinyl)anthraquinone; K₂[OsO₂(OH)4] / propan-1-ol; H₂O / 2 h / 20 °C

4.1: 77 percent / molecular sieves 4 Angstroem; BF₃*Et₂O / CH₂Cl₂ / -30 °C

With sodium hydroxide; tert-butylhypochlorite; 4 A molecular sieve; boron trifluoride diethyl etherate; tetra-(n-butyl)ammonium iodide; sodium carbonate; In propan-1-ol; dichloromethane; water; 3.2: Sharpless aminohydroxylation;
DOI:10.1002/anie.200462439