benzyl 4C-[(tert-butoxycarbonyl)amino]methyl-4-deoxy-α-D-arabinopyranoside

Base Information

• Chemical Name: benzyl 4C-[(tert-butoxycarbonyl)amino]methyl-4-deoxy-α-D-arabinopyranoside
• CAS No.: 478175-82-5
• Molecular Formula: C₁₈H₂₇NO₆
• Molecular Weight: 353.415
• Mol file: 478175-82-5.mol

Synonyms:benzyl 4C-[(tert-butoxycarbonyl)amino]methyl-4-deoxy-α-D-arabinopyranoside

Chemical Property of benzyl 4C-[(tert-butoxycarbonyl)amino]methyl-4-deoxy-α-D-arabinopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 4C-[(tert-butoxycarbonyl)amino]methyl-4-deoxy-α-D-arabinopyranoside

There total 10 articles about benzyl 4C-[(tert-butoxycarbonyl)amino]methyl-4-deoxy-α-D-arabinopyranoside 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: 85.0%

benzyl 4-C-cyano-4-deoxy-α-D-arabinoside (770735-90-5) + di-tert-butyl dicarbonate (24424-99-5) → benzyl 4C-[(tert-butoxycarbonyl)amino]methyl-4-deoxy-α-D-arabinopyranoside (478175-82-5)

Guidance literature:

benzyl 4-C-cyano-4-deoxy-α-D-arabinoside; With aluminium hydride; In tetrahydrofuran; at 0 ℃;

di-tert-butyl dicarbonate; With sodium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 5h;

DOI:10.1071/CH06241

Reference yield:

benzyl 2,3-O-isopropylidene-β-L-xylopyranoside (478175-66-5) → benzyl 4C-[(tert-butoxycarbonyl)amino]methyl-4-deoxy-α-D-arabinopyranoside (478175-82-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 90 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / 1 h / -30 - 20 °C

2.1: 80 percent / Bu₄NF / acetonitrile

3.1: 90 percent / camphor-10-sulfonic acid / methanol

4.1: AlH₃ / tetrahydrofuran / 0 °C

4.2: 85 percent / NaOH / H₂O; tetrahydrofuran / 5 h / 20 °C

With aluminium hydride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; acetonitrile;

DOI:10.1071/CH06241

Reference yield:

benzyl 4-cyano-4-deoxy-2,3-O-isopropylidene-α-D-arabinoside (478175-78-9) → benzyl 4C-[(tert-butoxycarbonyl)amino]methyl-4-deoxy-α-D-arabinopyranoside (478175-82-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 90 percent / camphor-10-sulfonic acid / methanol

2.1: AlH₃ / tetrahydrofuran / 0 °C

2.2: 85 percent / NaOH / H₂O; tetrahydrofuran / 5 h / 20 °C

With aluminium hydride; camphor-10-sulfonic acid; In tetrahydrofuran; methanol;

DOI:10.1071/CH06241

upstream raw materials:

benzyl 4-{[(tert-butoxycarbonyl)amino]methyl}-4-deoxy-2,3-O-isopropylidene-α-D-arabinoside

benzyl 4-C-cyano-4-deoxy-α-D-arabinoside

di-tert-butyl dicarbonate

benzyl 2,3-O-isopropylidene-β-L-xylopyranoside

Downstream raw materials:

(2R,3S,4R,5R)-5-Aminomethyl-2-benzyloxy-tetrahydro-pyran-3,4-diol

isofagomine

benzyl 4C-[(tert-butoxycarbonyl)amino]methyl-2,3-di-O-(tert-butyldimethylsilyl)-4-deoxy-α-D-arabinopyranoside

benzyl 4C-[(tert-butoxycarbonyl)amino]methyl-4-deoxy-2,3-bis-O-(trimethylsilyl)-α-D-arabinopyranoside

Refernces

• 1、 Best, Wayne M.,Macdonald, James M.,Skelton, Brian W.,Stick, Robert V.,Matthew,Tilbrook,White, Allan H.. "The synthesis of a carbohydrate-like dihydrooxazine and tetrahydrooxazine as putative inhibitors of glycoside hydrolases: A direct synthesis of isofagomine". . p. 857 - 865. Retrieved 2007/10/03.