methyl (5S)-5-O-benzyl-5-C-<(2S,5S,6R)-6-(benzyloxy)-5-<(tert-butyldimethylsilyl)oxymethyl>-3,4,5,6-tetrahydro-3-oxo-2H-1,4-diazepin-2-yl>-2,3-O-isopropylidene-β-D-ribofuranoside

Base Information

Chemical Name:methyl (5S)-5-O-benzyl-5-C-<(2S,5S,6R)-6-(benzyloxy)-5-<(tert-butyldimethylsilyl)oxymethyl>-3,4,5,6-tetrahydro-3-oxo-2H-1,4-diazepin-2-yl>-2,3-O-isopropylidene-β-D-ribofuranoside
CAS No.:143833-99-2
Molecular Formula:C₃₅H₅₀N₂O₈Si
Molecular Weight:654.876
Hs Code.:

methyl (5S)-5-O-benzyl-5-C-<(2S,5S,6R)-6-(benzyloxy)-5-<(tert-butyldimethylsilyl)oxymethyl>-3,4,5,6-tetrahydro-3-oxo-2H-1,4-diazepin-2-yl>-2,3-O-isopropylidene-β-D-ribofuranoside

Synonyms:methyl (5S)-5-O-benzyl-5-C-<(2S,5S,6R)-6-(benzyloxy)-5-<(tert-butyldimethylsilyl)oxymethyl>-3,4,5,6-tetrahydro-3-oxo-2H-1,4-diazepin-2-yl>-2,3-O-isopropylidene-β-D-ribofuranoside

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Chemical Property of methyl (5S)-5-O-benzyl-5-C-<(2S,5S,6R)-6-(benzyloxy)-5-<(tert-butyldimethylsilyl)oxymethyl>-3,4,5,6-tetrahydro-3-oxo-2H-1,4-diazepin-2-yl>-2,3-O-isopropylidene-β-D-ribofuranoside

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Technology Process of methyl (5S)-5-O-benzyl-5-C-<(2S,5S,6R)-6-(benzyloxy)-5-<(tert-butyldimethylsilyl)oxymethyl>-3,4,5,6-tetrahydro-3-oxo-2H-1,4-diazepin-2-yl>-2,3-O-isopropylidene-β-D-ribofuranoside

There total 16 articles about methyl (5S)-5-O-benzyl-5-C-<(2S,5S,6R)-6-(benzyloxy)-5-<(tert-butyldimethylsilyl)oxymethyl>-3,4,5,6-tetrahydro-3-oxo-2H-1,4-diazepin-2-yl>-2,3-O-isopropylidene-β-D-ribofuranoside 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: 36.0%

: methyl 6-azido-5-O-benzyl-N-<(1S,2R)-2-benzyloxy-1-(tert-butyldimethylsilyl)oxymethyl-2-formylethyl>-6-deoxy-2,3-O-isopropylidene-β-D-glycero-L-talo-heptofuranosiduronamide

: 143833-99-2
methyl (5S)-5-O-benzyl-5-C-<(2S,5S,6R)-6-(benzyloxy)-5-<(tert-butyldimethylsilyl)oxymethyl>-3,4,5,6-tetrahydro-3-oxo-2H-1,4-diazepin-2-yl>-2,3-O-isopropylidene-β-D-ribofuranoside

Guidance literature:: With hydrogen; palladium on activated charcoal; In ethyl acetate; for 48h;

Reference yield:

: 33985-40-9
(3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde

: 143833-99-2
methyl (5S)-5-O-benzyl-5-C-<(2S,5S,6R)-6-(benzyloxy)-5-<(tert-butyldimethylsilyl)oxymethyl>-3,4,5,6-tetrahydro-3-oxo-2H-1,4-diazepin-2-yl>-2,3-O-isopropylidene-β-D-ribofuranoside

Guidance literature:: Multi-step reaction with 12 steps

1: 1.) 18-crown-6-ether, potassium bis(trimethylsilyl)amide / 1.) THF, toluene, -78 deg C, 2.) THF, toluene, CH₂Cl₂, -78 deg C, 40 min

2: 81 percent / diisobutylaluminum hydride (DIBAL) / CH₂Cl₂ / 1.5 h / -20 - -10 °C

3: 77 percent / molecular sieves, L-(+)-diethyl tartarate , Ti(O-i-Pr)4, cumene hydroperoxide / CH₂Cl₂ / 24 h / -2 °C

4: 89 percent / NaN₃, NH₄Cl / 2-methoxy-ethanol; H₂O / 7 h / Heating

5: 98 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

6: 1.) NaH / 1.) THF, RT, 15 min, 2.) THF, RT, 4.5 h

7: 95 percent / tetra-butylammonium fluoride / dimethylformamide; tetrahydrofuran / 0.25 h / Ambient temperature

8: 1.) pyridinium dichromate (PDC), 2.) pyridinium trifluoroacetate / 1.) DMF, 14 h, 2.) DMF, 2 h

9: 60 percent / DCC, 1-hydroxybenzotriazole (HOBt) / tetrahydrofuran / 2 h / Ambient temperature

10: 63 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / CH₂Cl₂; H₂O / 2.5 h / Ambient temperature

11: 67 percent / CrO₃, pyridine / CH₂Cl₂ / 0.17 h / Ambient temperature

12: 36 percent / H₂ / 5percent Pd/C / ethyl acetate / 48 h

With pyridine; 1H-imidazole; chromium(VI) oxide; titanium(IV) isopropylate; dipyridinium dichromate; sodium azide; molecular sieve; 18-crown-6 ether; diethyl (2R,3R)-tartrate; Cumene hydroperoxide; tetrabutyl ammonium fluoride; hydrogen; pyridinium trifluroacetate; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; ammonium chloride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; 2-methoxy-ethanol; water; ethyl acetate; N,N-dimethyl-formamide;

Reference yield:

: 100-39-0
benzyl bromide

: 143833-99-2
methyl (5S)-5-O-benzyl-5-C-<(2S,5S,6R)-6-(benzyloxy)-5-<(tert-butyldimethylsilyl)oxymethyl>-3,4,5,6-tetrahydro-3-oxo-2H-1,4-diazepin-2-yl>-2,3-O-isopropylidene-β-D-ribofuranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) NaH / 1.) THF, 1 h, 2.) THF, 2.5 h

2: 87 percent / H₂ / 5percent Pd/C / ethyl acetate

3: 60 percent / DCC, 1-hydroxybenzotriazole (HOBt) / tetrahydrofuran / 2 h / Ambient temperature

4: 63 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / CH₂Cl₂; H₂O / 2.5 h / Ambient temperature

5: 67 percent / CrO₃, pyridine / CH₂Cl₂ / 0.17 h / Ambient temperature

6: 36 percent / H₂ / 5percent Pd/C / ethyl acetate / 48 h

With pyridine; chromium(VI) oxide; hydrogen; sodium hydride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate;