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

Base Information

• Chemical Name: ((2S,3R,4S,5S)-3,4,5,6-Tetrakis-benzyloxy-tetrahydro-pyran-2-yl)-methanol
• CAS No.: 221015-64-1
• Molecular Formula: C₃₄H₃₆O₆
• Molecular Weight: 540.656
• Mol file: 221015-64-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 15 articles about ((2S,3R,4S,5S)-3,4,5,6-Tetrakis-benzyloxy-tetrahydro-pyran-2-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:

(E)-3-(2-furanyl)-2-propen-1-ol (27393-97-1,79380-02-2) → ((2S,3R,4S,5S)-3,4,5,6-Tetrakis-benzyloxy-tetrahydro-pyran-2-yl)-methanol (221015-64-1)

Guidance literature:

Multi-step reaction with 14 steps

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

2: 94 percent / MeSO2NH2, AD-mix-β / 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: 99 percent / NaBH₄, CeCl₃*7H₂O / methanol / 0.42 h / 0 °C

6: 92 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) reflux, 12 h

7: 94 percent / NMO, OsO₄, H₂O / acetone; tetrahydrofuran / 3 h / Ambient temperature

8: 92 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) reflux, 5 h

9: 94 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature

10: Et₃N / CH₂Cl₂ / 3 h / Ambient temperature

11: LiI / tetrahydrofuran / 6 h / Heating

12: 97 percent / Zn, AcOH / 3 h / Ambient temperature

13: 85 percent / p-TsOH / benzene / 6 h / Heating

14: 1.) O₃, 2.) NaBH₄ / 1.) MeOH, CH₂Cl₂, -78 deg C, 10 min, 2.) MeOH, CH₂Cl₂, r.t., 20 min

With dmap; sodium tetrahydroborate; osmium(VIII) oxide; N-methyl-2-indolinone; cerium(III) chloride; methanesulfonamide; AD-mix-β; tetrabutyl ammonium fluoride; water; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; ozone; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium iodide; zinc; 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) → ((2S,3R,4S,5S)-3,4,5,6-Tetrakis-benzyloxy-tetrahydro-pyran-2-yl)-methanol (221015-64-1)

Guidance literature:

Multi-step reaction with 13 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: 99 percent / NaBH₄, CeCl₃*7H₂O / methanol / 0.42 h / 0 °C

5: 92 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) reflux, 12 h

6: 94 percent / NMO, OsO₄, H₂O / acetone; tetrahydrofuran / 3 h / Ambient temperature

7: 92 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) reflux, 5 h

8: 94 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature

9: Et₃N / CH₂Cl₂ / 3 h / Ambient temperature

10: LiI / tetrahydrofuran / 6 h / Heating

11: 97 percent / Zn, AcOH / 3 h / Ambient temperature

12: 85 percent / p-TsOH / benzene / 6 h / Heating

13: 1.) O₃, 2.) NaBH₄ / 1.) MeOH, CH₂Cl₂, -78 deg C, 10 min, 2.) MeOH, CH₂Cl₂, r.t., 20 min

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

DOI:10.1055/s-1999-3382

Reference yield:

(1S,5S,7R)-7-(tert-Butyl-dimethyl-silanyloxymethyl)-6,8-dioxa-bicyclo[3.2.1]oct-3-en-2-one (221015-46-9) → ((2S,3R,4S,5S)-3,4,5,6-Tetrakis-benzyloxy-tetrahydro-pyran-2-yl)-methanol (221015-64-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 99 percent / NaBH₄, CeCl₃*7H₂O / methanol / 0.42 h / 0 °C

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

3: 94 percent / NMO, OsO₄, H₂O / acetone; tetrahydrofuran / 3 h / Ambient temperature

4: 92 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) reflux, 5 h

5: 94 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature

6: Et₃N / CH₂Cl₂ / 3 h / Ambient temperature

7: LiI / tetrahydrofuran / 6 h / Heating

8: 97 percent / Zn, AcOH / 3 h / Ambient temperature

9: 85 percent / p-TsOH / benzene / 6 h / Heating

10: 1.) O₃, 2.) NaBH₄ / 1.) MeOH, CH₂Cl₂, -78 deg C, 10 min, 2.) MeOH, CH₂Cl₂, r.t., 20 min

With sodium tetrahydroborate; osmium(VIII) oxide; N-methyl-2-indolinone; cerium(III) chloride; tetrabutyl ammonium fluoride; water; sodium hydride; toluene-4-sulfonic acid; ozone; acetic acid; triethylamine; lithium iodide; zinc; In tetrahydrofuran; methanol; dichloromethane; acetone; benzene;

DOI:10.1055/s-1999-3382

upstream raw materials:

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

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

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

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

Downstream raw materials:

L-gulose