1,6-anhydro-3-deoxy-2-O-pivaloyl-3-p-toluenesulfonamido-β-D-altropyranose

Base Information

• Chemical Name: 1,6-anhydro-3-deoxy-2-O-pivaloyl-3-p-toluenesulfonamido-β-D-altropyranose
• CAS No.: 163356-94-3
• Molecular Formula: C₁₈H₂₅NO₇S
• Molecular Weight: 399.465

Synonyms:1,6-anhydro-3-deoxy-2-O-pivaloyl-3-p-toluenesulfonamido-β-D-altropyranose

Chemical Property of 1,6-anhydro-3-deoxy-2-O-pivaloyl-3-p-toluenesulfonamido-β-D-altropyranose

Chemical Property:

Purity/Quality:

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Technology Process of 1,6-anhydro-3-deoxy-2-O-pivaloyl-3-p-toluenesulfonamido-β-D-altropyranose

There total 2 articles about 1,6-anhydro-3-deoxy-2-O-pivaloyl-3-p-toluenesulfonamido-β-D-altropyranose 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: 53.4%

1,6-anhydro-3,4-dideoxy-2-O-pivaloyl-β-D-threo-hex-3-enopyranose (163356-90-9) → 2,2-Dimethyl-propionic acid (1R,2S,3R,4S,5R)-2,3-dihydroxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester + 1,6-anhydro-3-deoxy-2-O-pivaloyl-3-p-toluenesulfonamido-β-D-altropyranose (163356-94-3) + 2,2-Dimethyl-propionic acid (1S,2S,3R,4S,5R)-3-hydroxy-2-(toluene-4-sulfonylamino)-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester

Guidance literature:

With osmium(VIII) oxide; water; chloroamine-T; In tert-butyl alcohol; for 18h; Ambient temperature;

DOI:10.1016/0008-6215(94)00298-T

Reference yield: 53.4%

chloroamine-T (127-65-1) + 1,6-anhydro-3,4-dideoxy-2-O-pivaloyl-β-D-threo-hex-3-enopyranose (163356-90-9) → 2,2-Dimethyl-propionic acid (1R,2S,3R,4S,5R)-2,3-dihydroxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester + 1,6-anhydro-3-deoxy-2-O-pivaloyl-3-p-toluenesulfonamido-β-D-altropyranose (163356-94-3) + 2,2-Dimethyl-propionic acid (1S,2S,3R,4S,5R)-3-hydroxy-2-(toluene-4-sulfonylamino)-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester

Guidance literature:

With osmium(VIII) oxide; water; In tert-butyl alcohol; for 18h; Ambient temperature;

DOI:10.1016/0008-6215(94)00298-T

Reference yield: 96.5%

2,2-dimethoxy-propane (77-76-9) + 1,6-anhydro-3-deoxy-2-O-pivaloyl-3-p-toluenesulfonamido-β-D-altropyranose (163356-94-3) → 2,2-Dimethyl-propionic acid (1R,2S,6R,7S,8R)-4,4-dimethyl-5-(toluene-4-sulfonyl)-3,9,11-trioxa-5-aza-tricyclo[6.2.1.02,6]undec-7-yl ester (174272-12-9)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; for 1h; Heating;

DOI:10.1016/0008-6215(95)00261-8

upstream raw materials:

chloroamine-T

1,6-anhydro-3,4-dideoxy-2-O-pivaloyl-β-D-threo-hex-3-enopyranose

Downstream raw materials:

1,6-anhydro-3-deoxy-3-p-toluenesulfonamido-β-D-altropyranose

2,2-Dimethyl-propionic acid (1R,2S,6R,7S,8R)-4,4-dimethyl-5-(toluene-4-sulfonyl)-3,9,11-trioxa-5-aza-tricyclo[6.2.1.0^2,6]undec-7-yl ester

D-ribo-phytosphingosine

(2R,3S,4R)-3-hydroxy-4-hydroxymethyl-2-(p-tolylsulfonamido)-4-butanolide

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