O³-benzyl-O¹,O²-isopropylidene-O⁵,O⁶-bis-(toluene-4-sulfonyl)-α-D-glucofuranose

Base Information

• Chemical Name: O³-benzyl-O¹,O²-isopropylidene-O⁵,O⁶-bis-(toluene-4-sulfonyl)-α-D-glucofuranose
• CAS No.: 22331-18-6
• Molecular Formula: C₃₀H₃₄O₁₀S₂
• Molecular Weight: 618.726
• Mol file: 22331-18-6.mol

Synonyms:O³-benzyl-O¹,O²-isopropylidene-O⁵,O⁶-bis-(toluene-4-sulfonyl)-α-D-glucofuranose

Chemical Property of O³-benzyl-O¹,O²-isopropylidene-O⁵,O⁶-bis-(toluene-4-sulfonyl)-α-D-glucofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of O³-benzyl-O¹,O²-isopropylidene-O⁵,O⁶-bis-(toluene-4-sulfonyl)-α-D-glucofuranose

There total 8 articles about O³-benzyl-O¹,O²-isopropylidene-O⁵,O⁶-bis-(toluene-4-sulfonyl)-α-D-glucofuranose 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:

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol (22529-61-9) + p-toluenesulfonyl chloride (98-59-9) → (R)-2-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxyethyl 4-methylbenzenesulfonate (23313-03-3) + O3-benzyl-O1,O2-isopropylidene-O5,O6-bis-(toluene-4-sulfonyl)-α-D-glucofuranose (22331-18-6) + 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose (35781-78-3)

Guidance literature:

With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; In dichloromethane; for 0.5h; Ambient temperature;

DOI:10.1016/0008-6215(86)84022-8

Reference yield:

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol (22529-61-9) + p-toluenesulfonyl chloride (98-59-9) → O3-benzyl-O1,O2-isopropylidene-O5,O6-bis-(toluene-4-sulfonyl)-α-D-glucofuranose (22331-18-6)

Guidance literature:

With pyridine; chloroform;

DOI:10.1002/hlca.19460290120

Reference yield:

D-Glucose (2280-44-6) → O3-benzyl-O1,O2-isopropylidene-O5,O6-bis-(toluene-4-sulfonyl)-α-D-glucofuranose (22331-18-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) ZnCl₂, H₃PO₄, 2) NaH, 3) Bu₄NI

2: AcOH / 34 °C

3: pyridine

With pyridine; phosphoric acid; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; zinc(II) chloride;

DOI:10.1016/S0040-4039(00)61388-6

upstream raw materials:

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

p-toluenesulfonyl chloride

D-Glucose

benzyl bromide

Downstream raw materials:

3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose