Toluene-4-sulfonic acid 3-((2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-iodomethyl-tetrahydro-pyran-2-yl)-propyl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid 3-((2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-iodomethyl-tetrahydro-pyran-2-yl)-propyl ester
CAS No.:177078-63-6
Molecular Formula:C₁₆H₂₃IO₇S
Molecular Weight:486.325
Hs Code.:

Synonyms:Toluene-4-sulfonic acid 3-((2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-iodomethyl-tetrahydro-pyran-2-yl)-propyl ester

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Chemical Property of Toluene-4-sulfonic acid 3-((2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-iodomethyl-tetrahydro-pyran-2-yl)-propyl ester

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Technology Process of Toluene-4-sulfonic acid 3-((2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-iodomethyl-tetrahydro-pyran-2-yl)-propyl ester

There total 6 articles about Toluene-4-sulfonic acid 3-((2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-iodomethyl-tetrahydro-pyran-2-yl)-propyl 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: 90.0%

: 177078-73-8
Toluene-4-sulfonic acid 3-((2S,3S,4R,5S,6S)-3,4,5-tris-benzyloxy-6-iodomethyl-tetrahydro-pyran-2-yl)-propyl ester

: 177078-63-6
Toluene-4-sulfonic acid 3-((2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-iodomethyl-tetrahydro-pyran-2-yl)-propyl ester

Guidance literature:: With boron trifluoride diethyl etherate; ethanethiol; In dichloromethane; Ambient temperature;
DOI:10.1021/jo980088n

Reference yield:

: 53008-65-4,641635-63-4
methyl 2,3,4-tri-O-benzyl-D-glucopyranoside

: 177078-63-6
Toluene-4-sulfonic acid 3-((2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-iodomethyl-tetrahydro-pyran-2-yl)-propyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 96 percent / I₂, imidazole, Ph₃ / hexane / 3 h

2: 1.) Ac₂O, 2.) AcOH, 3.) (COCl)2, DMSO, Et₃N / 1.) THF, room temperature, 1 day, 2.) H₂O, 100 deg C, 1 day, 3.) CH₂Cl₂, -78 deg c to 0 deg C

3: 2.) BF₃*OEt₂, Et₃SiH / 1.) Et₂O, -78 deg C, 30 min, 2.) CH₃CN, 0 deg C, 30 min

4: 1.) diborane, 2.) aq. NaOH, aq. H₂O₂ / 1.) THF, 0 deg C, 1 h, 2.) EtOH, 30 min

5: 67 percent / pyridine / CH₂Cl₂ / 24 h / Ambient temperature

6: 90 percent / EtSH, BF₃*OEt₂ / CH₂Cl₂ / Ambient temperature

With pyridine; 1H-imidazole; triethylsilane; sodium hydroxide; oxalyl dichloride; boron trifluoride diethyl etherate; dihydrogen peroxide; iodine; phosphan; acetic anhydride; acetic acid; dimethyl sulfoxide; triethylamine; ethanethiol; diborane; In hexane; dichloromethane;
DOI:10.1021/jo980088n

Reference yield:

: 85716-43-4
methyl 6-deoxy-6-iodo-2,3,4-tri-O-benzyl-α-D-glucopyranoside

: 177078-63-6
Toluene-4-sulfonic acid 3-((2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-iodomethyl-tetrahydro-pyran-2-yl)-propyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) Ac₂O, 2.) AcOH, 3.) (COCl)2, DMSO, Et₃N / 1.) THF, room temperature, 1 day, 2.) H₂O, 100 deg C, 1 day, 3.) CH₂Cl₂, -78 deg c to 0 deg C

2: 2.) BF₃*OEt₂, Et₃SiH / 1.) Et₂O, -78 deg C, 30 min, 2.) CH₃CN, 0 deg C, 30 min

3: 1.) diborane, 2.) aq. NaOH, aq. H₂O₂ / 1.) THF, 0 deg C, 1 h, 2.) EtOH, 30 min

4: 67 percent / pyridine / CH₂Cl₂ / 24 h / Ambient temperature

5: 90 percent / EtSH, BF₃*OEt₂ / CH₂Cl₂ / Ambient temperature

With pyridine; triethylsilane; sodium hydroxide; oxalyl dichloride; boron trifluoride diethyl etherate; dihydrogen peroxide; acetic anhydride; acetic acid; dimethyl sulfoxide; triethylamine; ethanethiol; diborane; In dichloromethane;
DOI:10.1021/jo980088n