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

Base Information

Chemical Name:((1S,2R,3S,4R,5S,7R)-2,3,4-Tris-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-7-yl)-methanol
CAS No.:221015-98-1
Molecular Formula:C₂₈H₃₀O₆
Molecular Weight:462.543
Hs Code.:

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

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

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

There total 11 articles about ((1S,2R,3S,4R,5S,7R)-2,3,4-Tris-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-7-yl)-methanol 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: 99.0%

: 221015-96-9
tert-Butyl-dimethyl-((1S,2R,3S,4R,5S,7R)-2,3,4-tris-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-7-ylmethoxy)-silane

: 221015-98-1
((1S,2R,3S,4R,5S,7R)-2,3,4-Tris-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-7-yl)-methanol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 2h; Ambient temperature;
DOI:10.1055/s-1999-3382

Reference yield:

: 221015-42-5
tert-Butyl-((E)-3-furan-2-yl-allyloxy)-dimethyl-silane

: 221015-98-1
((1S,2R,3S,4R,5S,7R)-2,3,4-Tris-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-7-yl)-methanol

Guidance literature:: Multi-step reaction with 11 steps

1: 94 percent / MeSO2NH2, AD-mix-β / 2-methyl-propan-2-ol; H2O / 95 h / 0 °C

2: MCPBA, NaHCO₃ / CH₂Cl₂ / 3 h / Ambient temperature

3: p-TSOH / benzene / 5 h / Heating

4: 90 percent / H₂O₂, H₂O, NaOH / tetrahydrofuran / 0.17 h / Ambient temperature

5: 62 percent / NH₂NH₂*H₂O, AcOH / methanol / 3 h / Ambient temperature

6: 62 percent / PCC, NaOAc / CH₂Cl₂ / 10 h / Ambient temperature

7: 100 percent / NaBH₄, CeCl₃*7H₂O / methanol / 0.5 h / 0 °C

8: 92 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) reflux, 12 h

9: 91 percent / OsO₄, NMO, H₂O / acetone / 3 h / Ambient temperature

10: 90 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) reflux, 5 h

11: 99 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature

With sodium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; N-methyl-2-indolinone; cerium(III) chloride; methanesulfonamide; AD-mix-β; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; sodium acetate; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; hydrazine hydrate; acetic acid; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane; water; acetone; tert-butyl alcohol; benzene;
DOI:10.1055/s-1999-3382

Reference yield:

: 221015-90-3
(1S,2S,4R,6S,7R)-7-(tert-Butyl-dimethyl-silanyloxymethyl)-3,8,9-trioxa-tricyclo[4.2.1.0^2,4]nonan-5-one

: 221015-98-1
((1S,2R,3S,4R,5S,7R)-2,3,4-Tris-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-7-yl)-methanol

Guidance literature:: Multi-step reaction with 7 steps

1: 62 percent / NH₂NH₂*H₂O, AcOH / methanol / 3 h / Ambient temperature

2: 62 percent / PCC, NaOAc / CH₂Cl₂ / 10 h / Ambient temperature

3: 100 percent / NaBH₄, CeCl₃*7H₂O / methanol / 0.5 h / 0 °C

4: 92 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) reflux, 12 h

5: 91 percent / OsO₄, NMO, H₂O / acetone / 3 h / Ambient temperature

6: 90 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) reflux, 5 h

7: 99 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature

With sodium tetrahydroborate; osmium(VIII) oxide; N-methyl-2-indolinone; cerium(III) chloride; tetrabutyl ammonium fluoride; water; sodium acetate; sodium hydride; hydrazine hydrate; acetic acid; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane; acetone;
DOI:10.1055/s-1999-3382