3-O-benzyl-N-benzyloxycarbonyl-1,4-dideoxy-1,4-imino-D-arabinitol

Base Information

Chemical Name:3-O-benzyl-N-benzyloxycarbonyl-1,4-dideoxy-1,4-imino-D-arabinitol
CAS No.:131053-20-8
Molecular Formula:C₂₀H₂₃NO₅
Molecular Weight:357.406
Hs Code.:

Synonyms:3-O-benzyl-N-benzyloxycarbonyl-1,4-dideoxy-1,4-imino-D-arabinitol

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Chemical Property of 3-O-benzyl-N-benzyloxycarbonyl-1,4-dideoxy-1,4-imino-D-arabinitol

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Technology Process of 3-O-benzyl-N-benzyloxycarbonyl-1,4-dideoxy-1,4-imino-D-arabinitol

There total 12 articles about 3-O-benzyl-N-benzyloxycarbonyl-1,4-dideoxy-1,4-imino-D-arabinitol 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: 98.0%

: 131053-19-5
3-O-benzyl-N-benzyloxycarbonyl-2,5-dideoxy-2,5-imino-D-lyxose

: 131053-20-8
3-O-benzyl-N-benzyloxycarbonyl-1,4-dideoxy-1,4-imino-D-arabinitol

Guidance literature:: With sodium tetrahydroborate; In ethanol; water; for 0.25h;
DOI:10.1016/S0957-4166(00)86337-5

Reference yield:

: 101475-83-6
3-O-benzyl-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside

: 131053-20-8
3-O-benzyl-N-benzyloxycarbonyl-1,4-dideoxy-1,4-imino-D-arabinitol

Guidance literature:: Multi-step reaction with 10 steps

1: 87 percent / water, HOAc / methanol / 16 h / 50 °C

2: 1.) sodium periodate, 2.) NaBH₄ / 1.) ethanol, water, 3 h, 2.) RT, 8 h

3: 94 percent / pyridine / 2 h / 0 - 20 °C

4: 97 percent / sodium azide / dimethylformamide / 12 h / 70 °C

5: 44 percent / acetyl chloride / 36 h / 0 °C

6: 78 percent / pyridine / CH₂Cl₂ / 1 h / -50 - -30 °C

7: 92.5 percent / H₂ / 5percent Pd/C / ethyl acetate / 4 h / Ambient temperature

8: 90 percent / aq. sodium bicarbonate / diethyl ether / 12 h / Ambient temperature

9: 87 percent / aq. TFA

10: 98 percent / NaBH₄ / ethanol; H₂O / 0.25 h

With pyridine; sodium tetrahydroborate; sodium periodate; sodium azide; water; hydrogen; sodium hydrogencarbonate; acetic acid; acetyl chloride; trifluoroacetic acid; palladium on activated charcoal; In methanol; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0957-4166(00)86337-5

Reference yield:

: 131053-15-1
5-azido-3-O-benzyl-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose

: 131053-20-8
3-O-benzyl-N-benzyloxycarbonyl-1,4-dideoxy-1,4-imino-D-arabinitol

Guidance literature:: Multi-step reaction with 6 steps

1: 44 percent / acetyl chloride / 36 h / 0 °C

2: 78 percent / pyridine / CH₂Cl₂ / 1 h / -50 - -30 °C

3: 92.5 percent / H₂ / 5percent Pd/C / ethyl acetate / 4 h / Ambient temperature

4: 90 percent / aq. sodium bicarbonate / diethyl ether / 12 h / Ambient temperature

5: 87 percent / aq. TFA

6: 98 percent / NaBH₄ / ethanol; H₂O / 0.25 h

With pyridine; sodium tetrahydroborate; hydrogen; sodium hydrogencarbonate; acetyl chloride; trifluoroacetic acid; palladium on activated charcoal; In diethyl ether; ethanol; dichloromethane; water; ethyl acetate;
DOI:10.1016/S0957-4166(00)86337-5