3-O-(tri-O-acetyl-β-D-xylopyranosyl)-2-O-benzoyl-N-benzyloxycarbonyl-1,5-imino-1,4,5-trideoxy-D-threo-pentitol

Base Information

Chemical Name:3-O-(tri-O-acetyl-β-D-xylopyranosyl)-2-O-benzoyl-N-benzyloxycarbonyl-1,5-imino-1,4,5-trideoxy-D-threo-pentitol
CAS No.:266688-44-2
Molecular Formula:C₃₁H₃₅NO₁₂
Molecular Weight:613.618
Hs Code.:

Synonyms:3-O-(tri-O-acetyl-β-D-xylopyranosyl)-2-O-benzoyl-N-benzyloxycarbonyl-1,5-imino-1,4,5-trideoxy-D-threo-pentitol

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Chemical Property of 3-O-(tri-O-acetyl-β-D-xylopyranosyl)-2-O-benzoyl-N-benzyloxycarbonyl-1,5-imino-1,4,5-trideoxy-D-threo-pentitol

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Technology Process of 3-O-(tri-O-acetyl-β-D-xylopyranosyl)-2-O-benzoyl-N-benzyloxycarbonyl-1,5-imino-1,4,5-trideoxy-D-threo-pentitol

There total 10 articles about 3-O-(tri-O-acetyl-β-D-xylopyranosyl)-2-O-benzoyl-N-benzyloxycarbonyl-1,5-imino-1,4,5-trideoxy-D-threo-pentitol 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: 44.0%

: 128376-91-0,869848-87-3
2,3,4-tri-O-acetyl-α-D-xylopyranosyl trichloroacetimidate

: 266688-42-0
3-O-benzyl-N-benzyloxycarbonyl-1,4,5-trideoxy-1,5-imino-D-threo-pentitol

: 266688-44-2
3-O-(tri-O-acetyl-β-D-xylopyranosyl)-2-O-benzoyl-N-benzyloxycarbonyl-1,5-imino-1,4,5-trideoxy-D-threo-pentitol

Guidance literature:: With 4 A molecular sieve; boron trifluoride diethyl etherate; In 1,2-dichloro-ethane; for 2h;
DOI:10.1021/ja993805j

Reference yield:

: 266688-37-3
methyl 4-cyano-4-deoxy-D-threonate

: 266688-44-2
3-O-(tri-O-acetyl-β-D-xylopyranosyl)-2-O-benzoyl-N-benzyloxycarbonyl-1,5-imino-1,4,5-trideoxy-D-threo-pentitol

Guidance literature:: Multi-step reaction with 9 steps

1: pyridine / 1 h / 20 °C

2: 64 percent / H₂ / PtO₂ / methanol

3: 90 percent / Na; MeOH / 2 h / 20 °C

4: trimethylsilyl chloride / acetonitrile / 2 h / Heating

5: BH₃*Me₂S / dioxane / 2 h / Heating

6: 1M aq. HCl / 1 h / Heating

7: saturated aq. NaHCO₃

8: 44 percent / Et₃N / CH₂Cl₂ / 20 °C

9: 44 percent / BF₃*Et₂O; molecular sieves 4A / 1,2-dichloro-ethane / 2 h

With pyridine; hydrogenchloride; methanol; chloro-trimethyl-silane; dimethylsulfide borane complex; 4 A molecular sieve; boron trifluoride diethyl etherate; hydrogen; sodium; sodium hydrogencarbonate; triethylamine; platinum(IV) oxide; In 1,4-dioxane; methanol; dichloromethane; 1,2-dichloro-ethane; acetonitrile; 1: Acetylation / 2: Catalytic hydrogenation / 3: Deacetylation / 4: silylation / 5: Reduction / 6: desilylation / 7: Carboxylation / 8: Acylation / 9: Substitution;
DOI:10.1021/ja993805j

Reference yield:

: 266688-38-4
methyl 2,3-di-O-acetyl-4-cyano-4-deoxy-D-threonate

: 266688-44-2
3-O-(tri-O-acetyl-β-D-xylopyranosyl)-2-O-benzoyl-N-benzyloxycarbonyl-1,5-imino-1,4,5-trideoxy-D-threo-pentitol

Guidance literature:: Multi-step reaction with 8 steps

1: 64 percent / H₂ / PtO₂ / methanol

2: 90 percent / Na; MeOH / 2 h / 20 °C

3: trimethylsilyl chloride / acetonitrile / 2 h / Heating

4: BH₃*Me₂S / dioxane / 2 h / Heating

5: 1M aq. HCl / 1 h / Heating

6: saturated aq. NaHCO₃

7: 44 percent / Et₃N / CH₂Cl₂ / 20 °C

8: 44 percent / BF₃*Et₂O; molecular sieves 4A / 1,2-dichloro-ethane / 2 h

With hydrogenchloride; methanol; chloro-trimethyl-silane; dimethylsulfide borane complex; 4 A molecular sieve; boron trifluoride diethyl etherate; hydrogen; sodium; sodium hydrogencarbonate; triethylamine; platinum(IV) oxide; In 1,4-dioxane; methanol; dichloromethane; 1,2-dichloro-ethane; acetonitrile; 1: Catalytic hydrogenation / 2: Deacetylation / 3: silylation / 4: Reduction / 5: desilylation / 6: Carboxylation / 7: Acylation / 8: Substitution;
DOI:10.1021/ja993805j