(1R,2S,3R,4S,5R,7S)-2,3,4-Tris-benzyloxy-7-iodomethyl-6,8-dioxa-bicyclo[3.2.1]octane

Base Information

Chemical Name:(1R,2S,3R,4S,5R,7S)-2,3,4-Tris-benzyloxy-7-iodomethyl-6,8-dioxa-bicyclo[3.2.1]octane
CAS No.:221015-86-7
Molecular Formula:C₂₈H₂₉IO₅
Molecular Weight:572.44
Hs Code.:

Synonyms:(1R,2S,3R,4S,5R,7S)-2,3,4-Tris-benzyloxy-7-iodomethyl-6,8-dioxa-bicyclo[3.2.1]octane

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Chemical Property of (1R,2S,3R,4S,5R,7S)-2,3,4-Tris-benzyloxy-7-iodomethyl-6,8-dioxa-bicyclo[3.2.1]octane

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Technology Process of (1R,2S,3R,4S,5R,7S)-2,3,4-Tris-benzyloxy-7-iodomethyl-6,8-dioxa-bicyclo[3.2.1]octane

There total 13 articles about (1R,2S,3R,4S,5R,7S)-2,3,4-Tris-benzyloxy-7-iodomethyl-6,8-dioxa-bicyclo[3.2.1]octane 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:

: 27393-97-1,79380-02-2
(E)-3-(2-furanyl)-2-propen-1-ol

: 221015-86-7
(1R,2S,3R,4S,5R,7S)-2,3,4-Tris-benzyloxy-7-iodomethyl-6,8-dioxa-bicyclo[3.2.1]octane

Guidance literature:: Multi-step reaction with 12 steps

1: 95 percent / NaH, Bu₄NI / tetrahydrofuran / 1.) 0 deg C, 2.) r.t., 8 h

2: 74 percent / MeSO2NH2, AD-mix-β / 2-methyl-propan-2-ol; H2O / 46 h / 0 °C

3: MCPBA / CH₂Cl₂ / 3 h / Ambient temperature

4: p-TsOH / benzene / 10 h / Heating

5: 87 percent / H₂O₂, H₂O, NaOH / tetrahydrofuran / 0.5 h / Ambient temperature

6: 94 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 0.42 h / 0 °C

7: 93 percent / pyridine / H₂O / 22 h / Ambient temperature

8: 1.) BF₃*Et₂O, 2.) NaOMe / 1.) C₆H₆, r.t., 20 min, 2.) MeOH, r.t., 45 min

9: 98 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 2.) reflux, 8 h

10: 96 percent / H₂, CHCl₃ / 10percent Pd/C / ethanol / 1.5 h / Ambient temperature

11: Et₃N / CH₂Cl₂ / 1 h / 0 °C

12: LiI / tetrahydrofuran / 17 h / Heating

With pyridine; sodium hydroxide; sodium tetrahydroborate; cerium(III) chloride; chloroform; methanesulfonamide; AD-mix-β; boron trifluoride diethyl etherate; water; hydrogen; dihydrogen peroxide; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; tert-butyl alcohol; benzene;
DOI:10.1055/s-1999-3382

Reference yield:

: 221015-43-6
(E)-3-(2-Furyl)prop-2-enyl (2-naphthylmethyl) ether

: 221015-86-7
(1R,2S,3R,4S,5R,7S)-2,3,4-Tris-benzyloxy-7-iodomethyl-6,8-dioxa-bicyclo[3.2.1]octane

Guidance literature:: Multi-step reaction with 11 steps

1: 74 percent / MeSO2NH2, AD-mix-β / 2-methyl-propan-2-ol; H2O / 46 h / 0 °C

2: MCPBA / CH₂Cl₂ / 3 h / Ambient temperature

3: p-TsOH / benzene / 10 h / Heating

4: 87 percent / H₂O₂, H₂O, NaOH / tetrahydrofuran / 0.5 h / Ambient temperature

5: 94 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 0.42 h / 0 °C

6: 93 percent / pyridine / H₂O / 22 h / Ambient temperature

7: 1.) BF₃*Et₂O, 2.) NaOMe / 1.) C₆H₆, r.t., 20 min, 2.) MeOH, r.t., 45 min

8: 98 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 2.) reflux, 8 h

9: 96 percent / H₂, CHCl₃ / 10percent Pd/C / ethanol / 1.5 h / Ambient temperature

10: Et₃N / CH₂Cl₂ / 1 h / 0 °C

11: LiI / tetrahydrofuran / 17 h / Heating

With pyridine; sodium hydroxide; sodium tetrahydroborate; cerium(III) chloride; chloroform; methanesulfonamide; AD-mix-β; boron trifluoride diethyl etherate; water; hydrogen; dihydrogen peroxide; sodium methylate; sodium hydride; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; tert-butyl alcohol; benzene;
DOI:10.1055/s-1999-3382

Reference yield:

: 221015-45-8
(+)-(1S,2R)-1-(2-Furyl)-3-(2-naphthylmethyloxy)propane-1,2-diol

: 221015-86-7
(1R,2S,3R,4S,5R,7S)-2,3,4-Tris-benzyloxy-7-iodomethyl-6,8-dioxa-bicyclo[3.2.1]octane

Guidance literature:: Multi-step reaction with 10 steps

1: MCPBA / CH₂Cl₂ / 3 h / Ambient temperature

2: p-TsOH / benzene / 10 h / Heating

3: 87 percent / H₂O₂, H₂O, NaOH / tetrahydrofuran / 0.5 h / Ambient temperature

4: 94 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 0.42 h / 0 °C

5: 93 percent / pyridine / H₂O / 22 h / Ambient temperature

6: 1.) BF₃*Et₂O, 2.) NaOMe / 1.) C₆H₆, r.t., 20 min, 2.) MeOH, r.t., 45 min

7: 98 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 2.) reflux, 8 h

8: 96 percent / H₂, CHCl₃ / 10percent Pd/C / ethanol / 1.5 h / Ambient temperature

9: Et₃N / CH₂Cl₂ / 1 h / 0 °C

10: LiI / tetrahydrofuran / 17 h / Heating

With pyridine; sodium hydroxide; sodium tetrahydroborate; cerium(III) chloride; chloroform; boron trifluoride diethyl etherate; water; hydrogen; dihydrogen peroxide; sodium methylate; sodium hydride; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; benzene;
DOI:10.1055/s-1999-3382