1-p-tolyl-2,3,4-tri-O-benzyl-6-deoxy-1-thio-β-D-glucoheptopyranuronic acid

Base Information

Chemical Name:1-p-tolyl-2,3,4-tri-O-benzyl-6-deoxy-1-thio-β-D-glucoheptopyranuronic acid
CAS No.:1400906-93-5
Molecular Formula:C₃₅H₃₆O₆S
Molecular Weight:584.733
Hs Code.:

Synonyms:1-p-tolyl-2,3,4-tri-O-benzyl-6-deoxy-1-thio-β-D-glucoheptopyranuronic acid

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Chemical Property of 1-p-tolyl-2,3,4-tri-O-benzyl-6-deoxy-1-thio-β-D-glucoheptopyranuronic acid

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Technology Process of 1-p-tolyl-2,3,4-tri-O-benzyl-6-deoxy-1-thio-β-D-glucoheptopyranuronic acid

There total 3 articles about 1-p-tolyl-2,3,4-tri-O-benzyl-6-deoxy-1-thio-β-D-glucoheptopyranuronic acid 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: 63.0%

: 1400906-92-4
p-tolyl 2,3,4-tri-O-benzyl-6-deoxy-1-thio-β-D-glucoheptopyranoside

: 1400906-93-5
1-p-tolyl-2,3,4-tri-O-benzyl-6-deoxy-1-thio-β-D-glucoheptopyranuronic acid

Guidance literature:: With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; In dichloromethane; water; at 20 ℃; for 1h;
DOI:10.1021/jo300986c

Reference yield:

: 1400906-91-3
p-tolyl 2,3,4-tri-O-benzyl-6,7-dideoxy-1-thio-β-D-glucohept-6-enopyranoside

: 1400906-93-5
1-p-tolyl-2,3,4-tri-O-benzyl-6-deoxy-1-thio-β-D-glucoheptopyranuronic acid

Guidance literature:: Multi-step reaction with 2 steps

1: 9-bora-bicyclo[3.3.1]nonane; dihydrogen peroxide; sodium hydroxide / water; tetrahydrofuran / 0 - 20 °C

2: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 1 h / 20 °C

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; dihydrogen peroxide; 9-bora-bicyclo[3.3.1]nonane; sodium hydroxide; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/jo300986c

Reference yield:

: 479252-05-6
((2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-p-tolylsulfanyl-tetrahydro-pyran-2-yl)-methanol

: 1400906-93-5
1-p-tolyl-2,3,4-tri-O-benzyl-6-deoxy-1-thio-β-D-glucoheptopyranuronic acid

Guidance literature:: Multi-step reaction with 4 steps

1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 3 h / 20 °C

2: n-butyllithium / tetrahydrofuran / -70 - 0 °C

3: 9-bora-bicyclo[3.3.1]nonane; dihydrogen peroxide; sodium hydroxide / water; tetrahydrofuran / 0 - 20 °C

4: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 1 h / 20 °C

With n-butyllithium; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; dihydrogen peroxide; 9-bora-bicyclo[3.3.1]nonane; sodium hydroxide; In tetrahydrofuran; dichloromethane; water; 2: |Wittig Olefination;
DOI:10.1021/jo300986c