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

Base Information

• Chemical Name: (3R,4S,5R,6S)-2,3,4,5-Tetrakis-benzyloxy-6-vinyl-tetrahydro-pyran
• CAS No.: 221015-75-4
• Molecular Formula: C₃₅H₃₆O₅
• Molecular Weight: 536.668
• Mol file: 221015-75-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 17 articles about (3R,4S,5R,6S)-2,3,4,5-Tetrakis-benzyloxy-6-vinyl-tetrahydro-pyran 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%

(3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-vinyl-tetrahydro-pyran-2-ol + benzyl alcohol (100-51-6,185532-71-2) → (3R,4S,5R,6S)-2,3,4,5-Tetrakis-benzyloxy-6-vinyl-tetrahydro-pyran (221015-75-4)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 7h; Heating;

DOI:10.1055/s-1999-3382

Reference yield:

(E)-3-(2-furanyl)-2-propen-1-ol (27393-97-1,79380-02-2) → (3R,4S,5R,6S)-2,3,4,5-Tetrakis-benzyloxy-6-vinyl-tetrahydro-pyran (221015-75-4)

Guidance literature:

Multi-step reaction with 16 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: 84 percent / NMO, TPAP, sieves 4 Angstroem / CH₂Cl₂ / 1.5 h / Ambient temperature

14: 74 percent / DABCO / benzene / 15 h / Ambient temperature

15: 96 percent / DIBAL / CH₂Cl₂; toluene / 2 h / -78 °C

16: 88 percent / p-TsOH / benzene / 7 h / Heating

With 1,4-diaza-bicyclo[2.2.2]octane; dmap; sodium tetrahydroborate; osmium(VIII) oxide; N-methyl-2-indolinone; cerium(III) chloride; tetrapropylammonium perruthennate; methanesulfonamide; 4 A molecular sieve; AD-mix-β; tetrabutyl ammonium fluoride; water; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium iodide; zinc; In tetrahydrofuran; methanol; dichloromethane; water; acetone; toluene; 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) → (3R,4S,5R,6S)-2,3,4,5-Tetrakis-benzyloxy-6-vinyl-tetrahydro-pyran (221015-75-4)

Guidance literature:

Multi-step reaction with 15 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: 84 percent / NMO, TPAP, sieves 4 Angstroem / CH₂Cl₂ / 1.5 h / Ambient temperature

13: 74 percent / DABCO / benzene / 15 h / Ambient temperature

14: 96 percent / DIBAL / CH₂Cl₂; toluene / 2 h / -78 °C

15: 88 percent / p-TsOH / benzene / 7 h / Heating

With 1,4-diaza-bicyclo[2.2.2]octane; sodium tetrahydroborate; osmium(VIII) oxide; N-methyl-2-indolinone; cerium(III) chloride; tetrapropylammonium perruthennate; methanesulfonamide; 4 A molecular sieve; AD-mix-β; tetrabutyl ammonium fluoride; water; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium iodide; zinc; In tetrahydrofuran; methanol; dichloromethane; water; acetone; toluene; tert-butyl alcohol; benzene;

DOI:10.1055/s-1999-3382

upstream raw materials:

benzyl alcohol

(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:

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