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

Base Information

Chemical Name:methyl 3-O-allyl-5-O-benzyl-N-benzyloxycarbonyl-2,6-dideoxy-2,6-imino-α-L-gulofuranoside
CAS No.:161106-75-8
Molecular Formula:C₂₅H₂₉NO₆
Molecular Weight:439.508
Hs Code.:

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

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

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

There total 12 articles about methyl 3-O-allyl-5-O-benzyl-N-benzyloxycarbonyl-2,6-dideoxy-2,6-imino-α-L-gulofuranoside 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:

: 501-53-1,94274-21-2
benzyl chloroformate

: Trifluoro-methanesulfonic acid (2S,3R,4S,5R)-4-allyloxy-5-((S)-2-azido-1-benzyloxy-ethyl)-2-methoxy-tetrahydro-furan-3-yl ester

: 161106-75-8
methyl 3-O-allyl-5-O-benzyl-N-benzyloxycarbonyl-2,6-dideoxy-2,6-imino-α-L-gulofuranoside

Guidance literature:: Trifluoro-methanesulfonic acid (2S,3R,4S,5R)-4-allyloxy-5-((S)-2-azido-1-benzyloxy-ethyl)-2-methoxy-tetrahydro-furan-3-yl ester; With triphenylphosphine; In dichloromethane; at 20 - 45 ℃; for 4h;

With potassium carbonate; In tetrahydrofuran; methanol; water; at 20 ℃; for 96h;

benzyl chloroformate; In tetrahydrofuran; methanol; water; at 0 ℃; for 7h;
DOI:10.1016/S0040-4020(01)00642-1

Reference yield:

: 20316-77-2
(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

: 161106-75-8
methyl 3-O-allyl-5-O-benzyl-N-benzyloxycarbonyl-2,6-dideoxy-2,6-imino-α-L-gulofuranoside

Guidance literature:: Multi-step reaction with 9 steps

1.1: 175 g / acetic acid; H₂O / 16 h / 60 °C

2.1: CH₂Cl₂; pyridine / 1 h / -15 °C

3.1: 179 g / CH₂Cl₂; pyridine / 20 h / -15 - 20 °C

4.1: NaOMe / methanol; tetrahydrofuran; CH₂Cl₂ / 3 h / 20 °C

4.2: 78 percent / t-BuOK / dimethylformamide; tetrahydrofuran / 6 h / 0 - 20 °C

5.1: 3.70 g / NH₄Cl; NaN₃ / dimethylformamide; H₂O / 2 h / 80 °C

6.1: 3.84 g / n-tetrabutylammonium iodide; NaH / dimethylformamide / 2.5 h / 0 °C

7.1: 50 percent / 3 percent HCl / 18 h / 20 °C

8.1: 44.1 g / pyridine / CH₂Cl₂ / 1.6 h / -60 °C

9.1: PPh₃ / CH₂Cl₂ / 4 h / 20 - 45 °C

9.2: K₂CO₃ / H₂O; tetrahydrofuran; methanol / 96 h / 20 °C

9.3: 27.3 g / tetrahydrofuran; methanol; H₂O / 7 h / 0 °C

With pyridine; hydrogenchloride; sodium azide; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; ammonium chloride; triphenylphosphine; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)00642-1

Reference yield:

: 91882-92-7
3-O-allyl-1,2-O-isopropylidene-α-D-glucofuranose

: 161106-75-8
methyl 3-O-allyl-5-O-benzyl-N-benzyloxycarbonyl-2,6-dideoxy-2,6-imino-α-L-gulofuranoside

Guidance literature:: Multi-step reaction with 8 steps

1.1: CH₂Cl₂; pyridine / 1 h / -15 °C

2.1: 179 g / CH₂Cl₂; pyridine / 20 h / -15 - 20 °C

3.1: NaOMe / methanol; tetrahydrofuran; CH₂Cl₂ / 3 h / 20 °C

3.2: 78 percent / t-BuOK / dimethylformamide; tetrahydrofuran / 6 h / 0 - 20 °C

4.1: 3.70 g / NH₄Cl; NaN₃ / dimethylformamide; H₂O / 2 h / 80 °C

5.1: 3.84 g / n-tetrabutylammonium iodide; NaH / dimethylformamide / 2.5 h / 0 °C

6.1: 50 percent / 3 percent HCl / 18 h / 20 °C

7.1: 44.1 g / pyridine / CH₂Cl₂ / 1.6 h / -60 °C

8.1: PPh₃ / CH₂Cl₂ / 4 h / 20 - 45 °C

8.2: K₂CO₃ / H₂O; tetrahydrofuran; methanol / 96 h / 20 °C

8.3: 27.3 g / tetrahydrofuran; methanol; H₂O / 7 h / 0 °C

With pyridine; hydrogenchloride; sodium azide; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; ammonium chloride; triphenylphosphine; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)00642-1