Toluene-4-sulfonic acid (4aR,6S,7R,8aS)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (4aR,6S,7R,8aS)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester
• CAS No.: 14929-15-8
• Molecular Formula: C₂₁H₂₄O₇S
• Molecular Weight: 420.483
• Mol file: 14929-15-8.mol

Synonyms:Toluene-4-sulfonic acid (4aR,6S,7R,8aS)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Chemical Property of Toluene-4-sulfonic acid (4aR,6S,7R,8aS)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (4aR,6S,7R,8aS)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

There total 5 articles about Toluene-4-sulfonic acid (4aR,6S,7R,8aS)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester 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: 88.0%

methyl 4,6-O-benzylidene-3-deoxy-ribo-hexopyranoside (40773-64-6) + p-toluenesulfonyl chloride (98-59-9) → Toluene-4-sulfonic acid (4aR,6S,7R,8aS)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (14929-15-8)

Guidance literature:

With pyridine;

DOI:10.1016/S0040-4039(00)94943-8

Reference yield:

p-toluenesulfonyl chloride (98-59-9) + methyl 3-deoxy-4,6-O-phenylmethylene-α-D-arabinohexopyranoside (72904-78-0) → methyl-[O4,O6-((R)-benzylidene)-O2-(toluene-4-sulfonyl)-α-D-arabino-3-deoxy-hexopyranoside] (14929-14-7,14929-15-8,14929-16-9,79297-68-0)

Guidance literature:

With pyridine;

DOI:10.1039/jr9540004511 DOI:10.1002/hlca.19460290510

Reference yield:

benzaldehyde (100-52-7) → methyl-[O4,O6-((R)-benzylidene)-O2-(toluene-4-sulfonyl)-α-D-arabino-3-deoxy-hexopyranoside] (14929-14-7,14929-15-8,14929-16-9,79297-68-0)

Guidance literature:

Multi-step reaction with 2 steps

1: zinc chloride

2: pyridine

With pyridine; zinc(II) chloride;

DOI:10.1002/hlca.19460290510

upstream raw materials:

p-toluenesulfonyl chloride

methyl 3-deoxy-4,6-O-phenylmethylene-α-D-arabinohexopyranoside

benzaldehyde

methyl 2,3-anhydro-4,6-O-benzilidene-α-D-mannopyranoside

Downstream raw materials:

(2R,4aR,6S,8aS)-(+)-6-methoxy-2-phenyl-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxine

methyl 2-azido-4,6-O-benzylidene-2,3-dideoxy-α-D-arabino-hexopyranoside

(2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)pyrrolidine-2-carboxylic acid

((2S,3S,5S,6R)-5-Hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester