6-O-Trityl-1,2,3,4-tetra-O-benzyl-α-D-mannopyranose

Base Information

• Chemical Name: 6-O-Trityl-1,2,3,4-tetra-O-benzyl-α-D-mannopyranose
• CAS No.: 78561-22-5
• Molecular Formula: C53H50 O6
• Molecular Weight: 782.976
• Mol file: 78561-22-5.mol

Synonyms:6-O-Trityl-1,2,3,4-tetra-O-benzyl-α-D-mannopyranose

Chemical Property of 6-O-Trityl-1,2,3,4-tetra-O-benzyl-α-D-mannopyranose

Chemical Property:

• PSA: 55.38000
• LogP: 10.69300

Purity/Quality:

97% ^*data from raw suppliers

1,2,3,4-Tetra-O-benzyl-6-O-trityl-a-D-mannopyranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 6-O-Trityl-1,2,3,4-tetra-O-benzyl-α-D-mannopyranose

There total 8 articles about 6-O-Trityl-1,2,3,4-tetra-O-benzyl-α-D-mannopyranose 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: 99.0%

benzyl 6-O-triphenylmethyl-α-D-mannopyranoside (77455-30-2) + benzyl bromide (100-39-0) → benzyl 2,3,4-tri-O-benzyl-6-O-triphenylmethyl-α-D-mannopyranoside (78561-22-5,39687-22-4)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1073/pnas.1002717107

Reference yield:

D-Mannose (530-26-7) → benzyl 2,3,4-tri-O-benzyl-6-O-triphenylmethyl-α-D-mannopyranoside (78561-22-5,39687-22-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 66 percent / acetyl chloride / 0 deg C, RT, 4 d

2: 85 percent / pyridine, 4-dimethylaminopyridine / 72 h / 40 °C

3: sodium hydroxide / dimethylsulfoxide / 1.5 h / Ambient temperature

With pyridine; dmap; sodium hydroxide; acetyl chloride; In dimethyl sulfoxide;

DOI:10.1016/0008-6215(86)80013-1

Reference yield:

(2S,3S,4S,5S,6R)-2-benzyloxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol (15548-45-5) → benzyl 2,3,4-tri-O-benzyl-6-O-triphenylmethyl-α-D-mannopyranoside (78561-22-5,39687-22-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / pyridine, 4-dimethylaminopyridine / 72 h / 40 °C

2: sodium hydroxide / dimethylsulfoxide / 1.5 h / Ambient temperature

With pyridine; dmap; sodium hydroxide; In dimethyl sulfoxide;

DOI:10.1016/0008-6215(86)80013-1

upstream raw materials:

benzyl 6-O-triphenylmethyl-α-D-mannopyranoside

benzyl bromide

benzyl chloride

(2S,3S,4S,5S,6R)-2-benzyloxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol

Downstream raw materials:

benzyl 2,3,4-tri-O-benzyl-α-D-mannopyranuronic acid

benzyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-O-(2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1<*>6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside

benzyl O-β-D-galactopyranosyl-(1<*>4)-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1<*>6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside

benzyl 6,7-di-O-acetyl-2,3,4-tri-O-benzyl-α-D-glycero-D-manno-heptopyranoside

Refernces

• 1、 Ma, Jing,Wang, Qingpeng,Huang, Zhonglv,Yang, Xiande,Nie, Quandeng,Hao, Wenpei,Wang, Peng George,Wang, Xin. "Glycosylated Platinum(IV) Complexes as Substrates for Glucose Transporters (GLUTs) and Organic Cation Transporters (OCTs) Exhibited Cancer Targeting and Human Serum Albumin Binding Properties for Drug Delivery". supporting information. p. 5736 - 5748. Retrieved 2017/07/22.
• 2、 Dziewiszek, Krzysztof,Zamoiski, Aleksander. "NEW SYNTHESES OF D- AND L-GLYCERO-D-MANNO-HEPTOSES". . p. 163 - 172. Retrieved 2007/10/02.