neopentyl 2,3,4-tri-O-benzyl-5-benzyloxycarbonylamino-5-deoxy-β-D-arabinopyranoside

Base Information

• Chemical Name: neopentyl 2,3,4-tri-O-benzyl-5-benzyloxycarbonylamino-5-deoxy-β-D-arabinopyranoside
• CAS No.: 161418-75-3
• Molecular Formula: C₃₉H₄₅NO₆
• Molecular Weight: 623.789
• Mol file: 161418-75-3.mol

Synonyms:neopentyl 2,3,4-tri-O-benzyl-5-benzyloxycarbonylamino-5-deoxy-β-D-arabinopyranoside

Chemical Property of neopentyl 2,3,4-tri-O-benzyl-5-benzyloxycarbonylamino-5-deoxy-β-D-arabinopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of neopentyl 2,3,4-tri-O-benzyl-5-benzyloxycarbonylamino-5-deoxy-β-D-arabinopyranoside

There total 14 articles about neopentyl 2,3,4-tri-O-benzyl-5-benzyloxycarbonylamino-5-deoxy-β-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: 100.0%

2,2-dimethyl-propanol-1 (75-84-3) + (2S,3S,4R,5R)-2-Acetoxy-3,4,5-tris-benzyloxy-piperidine-1-carboxylic acid benzyl ester → neopentyl 2,3,4-tri-O-benzyl-5-benzyloxycarbonylamino-5-deoxy-β-D-arabinopyranoside (161418-75-3)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at 0 ℃; for 1.08333h;

DOI:10.1016/S0008-6215(99)00253-0

Reference yield:

2,3,4-tri-O-benzyl-5-benzyloxycarbonylamino-5-deoxy-D-arabinitol (161512-13-6) → neopentyl 2,3,4-tri-O-benzyl-5-benzyloxycarbonylamino-5-deoxy-β-D-arabinopyranoside (161418-75-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / Me₂SO; (COCl)2; Et₃N / CH₂Cl₂ / 0.67 h / -78 °C

2: pyridine

3: 100 percent / 4 Angstroem molecular sieves; Me₃SiOTf / CH₂Cl₂ / 1.08 h / 0 °C

With oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; dimethyl sulfoxide; triethylamine; In pyridine; dichloromethane; 1: Swern oxidation, hemiaminal construction / 2: Acetylation / 3: Substitution;

DOI:10.1016/S0008-6215(99)00253-0

Reference yield:

5-azido-5-deoxy-D-arabinofuranose → neopentyl 2,3,4-tri-O-benzyl-5-benzyloxycarbonylamino-5-deoxy-β-D-arabinopyranoside (161418-75-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 100 percent / NaBH₄ / methanol / 0.5 h / 20 °C

2: 83 percent / pyridine / 48 h / 20 °C

3: 95 percent / NaH / dimethylformamide / 3.5 h / 0 - 20 °C

4: 63 percent / AcOH 70 percent / H₂O / 4 h / 60 °C

5: LiAlH₄ / tetrahydrofuran / 20 °C

6: 95 percent / tetrahydrofuran / 0 °C

7: 95 percent / Me₂SO; (COCl)2; Et₃N / CH₂Cl₂ / 0.67 h / -78 °C

8: pyridine

9: 100 percent / 4 Angstroem molecular sieves; Me₃SiOTf / CH₂Cl₂ / 1.08 h / 0 °C

With sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium hydride; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; 1: Reduction / 2: tritylation / 3: benzylation / 4: Elimination / 5: Reduction / 6: Substitution / 7: Swern oxidation, hemiaminal construction / 8: Acetylation / 9: Substitution;

DOI:10.1016/S0008-6215(99)00253-0

upstream raw materials:

2,2-dimethyl-propanol-1

2,3,4-tri-O-benzyl-5-benzyloxycarbonylamino-5-deoxy-D-arabinitol

1,2,3-tri-O-acetyl-5-hydroxy-D-arabinofuranose

1,2,3-tri-O-acetyl-5-azido-5-deoxy-D-arabinofuranose

Refernces

• 1、 Suzuki,Hashimoto. "Synthesis of ethyl 2-acetamido-6-S-(5-amino-5-deoxy-β-D- arabinopyranosyl)-2-deoxy-1,6-dithio-β-D-glucopyranoside: A sulfur-linked 5- amino-5-deoxyglycopyranosyl disaccharide". . p. 14 - 27. Retrieved 2007/10/03.