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

Base Information

• Chemical Name: methyl 3-O-allyl-5-O-benzyl-N-benzyloxycarbonyl-2,6-dideoxy-2,6-imino-β-L-gulofuranoside
• CAS No.: 372493-94-2
• Molecular Formula: C₂₅H₂₉NO₆
• Molecular Weight: 439.508

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

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

Chemical Property:

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

There total 11 articles about methyl 3-O-allyl-5-O-benzyl-N-benzyloxycarbonyl-2,6-dideoxy-2,6-imino-β-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:

benzyl chloroformate (501-53-1,94274-21-2) + Trifluoro-methanesulfonic acid (2R,3R,4S,5R)-4-allyloxy-5-((S)-2-azido-1-benzyloxy-ethyl)-2-methoxy-tetrahydro-furan-3-yl ester → methyl 3-O-allyl-5-O-benzyl-N-benzyloxycarbonyl-2,6-dideoxy-2,6-imino-β-L-gulofuranoside (372493-94-2)

Guidance literature:

Trifluoro-methanesulfonic acid (2R,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 2.5h;

With potassium carbonate; In tetrahydrofuran; methanol; water; at 20 ℃; for 48h;

benzyl chloroformate; In tetrahydrofuran; methanol; water; at 0 ℃; for 1h;

DOI:10.1016/S0040-4020(01)00642-1

Reference yield:

(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 (20316-77-2) → methyl 3-O-allyl-5-O-benzyl-N-benzyloxycarbonyl-2,6-dideoxy-2,6-imino-β-L-gulofuranoside (372493-94-2)

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: 47 percent / 3 percent HCl / 18 h / 20 °C

8.1: 880 mg / pyridine / CH₂Cl₂ / 0.75 h / -60 °C

9.1: PPh₃ / CH₂Cl₂ / 2.5 h / 20 - 45 °C

9.2: K₂CO₃ / H₂O; tetrahydrofuran; methanol / 48 h / 20 °C

9.3: 64 mg / tetrahydrofuran; methanol; H₂O / 1 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:

3-O-allyl-1,2-O-isopropylidene-α-D-glucofuranose (91882-92-7) → methyl 3-O-allyl-5-O-benzyl-N-benzyloxycarbonyl-2,6-dideoxy-2,6-imino-β-L-gulofuranoside (372493-94-2)

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: 47 percent / 3 percent HCl / 18 h / 20 °C

7.1: 880 mg / pyridine / CH₂Cl₂ / 0.75 h / -60 °C

8.1: PPh₃ / CH₂Cl₂ / 2.5 h / 20 - 45 °C

8.2: K₂CO₃ / H₂O; tetrahydrofuran; methanol / 48 h / 20 °C

8.3: 64 mg / tetrahydrofuran; methanol; H₂O / 1 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

upstream raw materials:

benzyl chloroformate

(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

3-O-allyl-1,2-O-isopropylidene-α-D-glucofuranose

3-O-allyl-5,6-anhydro-1,2-O-isopropylidene-β-L-idofuranose

Downstream raw materials:

2,3-di-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-glucitol

4-O-allyl-N-benzyloxycarbonyl-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-1,5-dideoxy-1,5-imino-D-gulcitol

benzyl 3-O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-N-benzyloxycarbonyl-4,5-di-O-benzyl-2,6-dideoxy-2,6-imino-L-gulonate

benzyl 3-O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-α-D-glucopyranosyl)-N-benzyloxycarbonyl-4,5-di-O-benzyl-2,6-dideoxy-2,6-imino-L-gulonate

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