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

Base Information

• Chemical Name: ((1R,2R,3R,4R,5R,7S)-2,3,4-Tris-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-7-yl)-methanol
• CAS No.: 221015-57-2
• Molecular Formula: C₂₈H₃₀O₆
• Molecular Weight: 462.543
• Mol file: 221015-57-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about ((1R,2R,3R,4R,5R,7S)-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:

tert-Butyl-dimethyl-((1R,2R,3R,4R,5R,7S)-2,3,4-tris-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-7-ylmethoxy)-silane (221015-55-0) → ((1R,2R,3R,4R,5R,7S)-2,3,4-Tris-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-7-yl)-methanol (221015-57-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 2h; Yield given; Ambient temperature;

DOI:10.1055/s-1999-3382

Reference yield:

(E)-3-(2-furanyl)-2-propen-1-ol (27393-97-1,79380-02-2) → ((1R,2R,3R,4R,5R,7S)-2,3,4-Tris-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-7-yl)-methanol (221015-57-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 98 percent / DMAP / CH₂Cl₂ / 4 h / Ambient temperature

2: MeSO2NH2, AD-mix-α / 2-methyl-propan-2-ol; H2O / 95 h / 0 °C

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

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

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

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

7: NMO, OsO₄, H₂O / acetone; tetrahydrofuran / 3 h / Ambient temperature

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

9: TBAF / tetrahydrofuran / 2 h / Ambient temperature

With dmap; sodium tetrahydroborate; AD-mix-α; osmium(VIII) oxide; N-methyl-2-indolinone; cerium(III) chloride; methanesulfonamide; tetrabutyl ammonium fluoride; water; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; water; acetone; tert-butyl alcohol; benzene;

DOI:10.1055/s-1999-3382

Reference yield:

tert-Butyl-((E)-3-furan-2-yl-allyloxy)-dimethyl-silane (221015-42-5) → ((1R,2R,3R,4R,5R,7S)-2,3,4-Tris-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-7-yl)-methanol (221015-57-2)

Guidance literature:

Multi-step reaction with 8 steps

1: MeSO2NH2, AD-mix-α / 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: NaBH₄, CeCl₃*7H₂O / methanol / 0.42 h / 0 °C

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

6: NMO, OsO₄, H₂O / acetone; tetrahydrofuran / 3 h / Ambient temperature

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

8: TBAF / tetrahydrofuran / 2 h / Ambient temperature

With sodium tetrahydroborate; AD-mix-α; osmium(VIII) oxide; N-methyl-2-indolinone; cerium(III) chloride; methanesulfonamide; tetrabutyl ammonium fluoride; water; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; water; acetone; tert-butyl alcohol; benzene;

DOI:10.1055/s-1999-3382

upstream raw materials:

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

(E)-3-(2-furanyl)-2-propen-1-ol

tert-Butyl-((E)-3-furan-2-yl-allyloxy)-dimethyl-silane

(1R,5R,7S)-7-(tert-Butyl-dimethyl-silanyloxymethyl)-6,8-dioxa-bicyclo[3.2.1]oct-3-en-2-one

Downstream raw materials:

((2R,3S,4R,5R)-3,4,5,6-Tetrakis-benzyloxy-tetrahydro-pyran-2-yl)-methanol

(3R,4R,5S,6R)-2,3,4,5-Tetrakis-benzyloxy-6-vinyl-tetrahydro-pyran

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

D-gulose

Refernces