Toluene-4-sulfonic acid (1S,2S,3S,4R,5R)-2-allyl-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (1S,2S,3S,4R,5R)-2-allyl-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester
• CAS No.: 74878-90-3
• Molecular Formula: C₁₆H₂₀O₆S
• Molecular Weight: 340.397
• Mol file: 74878-90-3.mol

Synonyms:Toluene-4-sulfonic acid (1S,2S,3S,4R,5R)-2-allyl-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester

Chemical Property of Toluene-4-sulfonic acid (1S,2S,3S,4R,5R)-2-allyl-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (1S,2S,3S,4R,5R)-2-allyl-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester

There total 1 articles about Toluene-4-sulfonic acid (1S,2S,3S,4R,5R)-2-allyl-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-4-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%

1,6:3,4-dianhydro-2-O-tosyl-D-galactose (6167-32-4) + allylmagnesium bromide (2622-05-1) → Toluene-4-sulfonic acid (1S,2S,3S,4R,5R)-2-allyl-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester (74878-90-3)

Guidance literature:

With copper(l) iodide; In tetrahydrofuran; at 0 ℃; for 20h;

DOI:10.1039/c39800000228

Reference yield:

Toluene-4-sulfonic acid (1S,2S,3S,4R,5R)-2-allyl-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester (74878-90-3) → C41H45(2)HO9

Guidance literature:

Multi-step reaction with 19 steps

1: Na-Hg, methanol / 12 h / Ambient temperature

2: 1) NaH, 2) imidazole / n-Bu₄NI / 1) THF, DMF, 0 deg C, 30 min., 2) r.t., 24 h

3: N-methylmorpholine N-oxide (NMMO), OsO₄ / acetone; H₂O / 6 h / Ambient temperature

4: NaIO₄ / methanol; H₂O / 2 h / Ambient temperature

5: NaBH₄ / methanol; diethyl ether / 1 h / 0 °C

6: 98 percent / Et₃N / diethyl ether / 3 h / 0 °C

7: 83 percent / NaI, NaHCO₃ / acetone / 12 h

8: 72 percent / dimethylformamide / 4 h / 110 °C

9: 1) n-BuLi / 1) THF, 0 deg C, 15 min., 2) 0 deg C, 30 min.

10: N,N'-bis(mesitylmethyl)-(R,R')-1,2-diphenyl-1,2-diaminoethane, OsO₄ / CH₂Cl₂ / -80 °C

11: 1) NaH / 1) THF, 0 deg C, 2) r.t.

12: 1) (COCl)2, DMSO, 2) Et₃N

13: 4N HCl / tetrahydrofuran

14: pyridine / 0 °C

15: BF₃*Et₂O / 0 °C

16: n-Bu₃SnH, AIBN / toluene / 110 °C

17: 1) (COCl)2, DMSO, 2) Et₃N

18: BH₃*Et₃N / tetrahydrofuran

19: NaOCH₃ / methanol

With pyridine; 1H-imidazole; hydrogenchloride; methanol; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; n-butyllithium; sodium amalgam; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); 1,2-diphenyl-N,N'-bis[(2,4,6-trimethylphenyl)methyl]-1,2-diaminoethane; triethylamine-borane; boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; sodium methylate; sodium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; sodium iodide; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1021/jo00028a017

Reference yield:

Toluene-4-sulfonic acid (1S,2S,3S,4R,5R)-2-allyl-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester (74878-90-3) → C41H45(2)HO9

Guidance literature:

Multi-step reaction with 17 steps

1: Na-Hg, methanol / 12 h / Ambient temperature

2: 1) NaH, 2) imidazole / n-Bu₄NI / 1) THF, DMF, 0 deg C, 30 min., 2) r.t., 24 h

3: N-methylmorpholine N-oxide (NMMO), OsO₄ / acetone; H₂O / 6 h / Ambient temperature

4: NaIO₄ / methanol; H₂O / 2 h / Ambient temperature

5: NaBH₄ / methanol; diethyl ether / 1 h / 0 °C

6: 98 percent / Et₃N / diethyl ether / 3 h / 0 °C

7: 83 percent / NaI, NaHCO₃ / acetone / 12 h

8: 72 percent / dimethylformamide / 4 h / 110 °C

9: 1) n-BuLi / 1) THF, 0 deg C, 15 min., 2) 0 deg C, 30 min.

10: N,N'-bis(mesitylmethyl)-(R,R')-1,2-diphenyl-1,2-diaminoethane, OsO₄ / CH₂Cl₂ / -80 °C

11: 1) NaH / 1) THF, 0 deg C, 2) r.t.

12: 1) (COCl)2, DMSO, 2) Et₃N

13: 4N HCl / tetrahydrofuran

14: pyridine / 0 °C

15: BF₃*Et₂O / 0 °C

16: n-Bu₃SnH, AIBN / toluene / 110 °C

17: NaOCH₃ / methanol

With pyridine; 1H-imidazole; hydrogenchloride; methanol; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; n-butyllithium; sodium amalgam; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); 1,2-diphenyl-N,N'-bis[(2,4,6-trimethylphenyl)methyl]-1,2-diaminoethane; boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; sodium methylate; sodium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; sodium iodide; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1021/jo00028a017

upstream raw materials:

1,6:3,4-dianhydro-2-O-tosyl-D-galactose

allylmagnesium bromide

Downstream raw materials:

1,6-anhydro-2,4-dideoxy-2-N,4-(propane-1,3-diyl)-2-(tosylamino)-β-D-glucopyranose

1,6-anhydro-2-azido-2,4-dideoxy-4-[3-(tosyloxy)propyl]-β-D-glucopyranose

1,6-anhydro-2,4-dideoxy-2-(tosylamino)-4-[3-(tosyloxy)propyl]-β-D-glucopyranose

(1S,2R,3S,4R,5R)-3,4-Bis-benzyloxy-2-[(Z)-(4R,5S)-4,5-bis-benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pent-2-enyl]-6,8-dioxa-bicyclo[3.2.1]octane