<5R-(5R*,6R*,7R*,8S*,9S*,10R*,12S*,13S*,14R*,15R*,16S*)>-5-Ethyl-2,2,3,3,6,8,10,12,14,16,20,20-dodecamethyl-19,19-diphenyl-7,9,13,15-tetrakis(phenylmethoxy)-4,18-dioxa-3,19-disilaheneicosane (Protected Hexaol 41)

Base Information

• Chemical Name: <5R-(5R*,6R*,7R*,8S*,9S*,10R*,12S*,13S*,14R*,15R*,16S*)>-5-Ethyl-2,2,3,3,6,8,10,12,14,16,20,20-dodecamethyl-19,19-diphenyl-7,9,13,15-tetrakis(phenylmethoxy)-4,18-dioxa-3,19-disilaheneicosane (Protected Hexaol 41)
• CAS No.: 123992-33-6
• Molecular Formula: C₇₁H₁₀₀O₆Si₂
• Molecular Weight: 1105.74
• Mol file: 123992-33-6.mol

Synonyms:<5R-(5R*,6R*,7R*,8S*,9S*,10R*,12S*,13S*,14R*,15R*,16S*)>-5-Ethyl-2,2,3,3,6,8,10,12,14,16,20,20-dodecamethyl-19,19-diphenyl-7,9,13,15-tetrakis(phenylmethoxy)-4,18-dioxa-3,19-disilaheneicosane (Protected Hexaol 41)

Chemical Property of <5R-(5R*,6R*,7R*,8S*,9S*,10R*,12S*,13S*,14R*,15R*,16S*)>-5-Ethyl-2,2,3,3,6,8,10,12,14,16,20,20-dodecamethyl-19,19-diphenyl-7,9,13,15-tetrakis(phenylmethoxy)-4,18-dioxa-3,19-disilaheneicosane (Protected Hexaol 41)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <5R-(5R*,6R*,7R*,8S*,9S*,10R*,12S*,13S*,14R*,15R*,16S*)>-5-Ethyl-2,2,3,3,6,8,10,12,14,16,20,20-dodecamethyl-19,19-diphenyl-7,9,13,15-tetrakis(phenylmethoxy)-4,18-dioxa-3,19-disilaheneicosane (Protected Hexaol 41)

There total 29 articles about <5R-(5R*,6R*,7R*,8S*,9S*,10R*,12S*,13S*,14R*,15R*,16S*)>-5-Ethyl-2,2,3,3,6,8,10,12,14,16,20,20-dodecamethyl-19,19-diphenyl-7,9,13,15-tetrakis(phenylmethoxy)-4,18-dioxa-3,19-disilaheneicosane (Protected Hexaol 41) 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: 96.0%

<3R-(3R*,4S*,5S*,6S*,8R*,10S*,11S*,12R*,13R*,14S*)>-153-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>-4,6,8,10,12,14-hexamethyl-5,7,11,13-tetrakis(phenylmethoxy)-3-pentadecanol (Alcohol 2) (123992-29-0) + tert-butyldimethylsilyl triflate (133732-91-9) → <5R-(5R*,6R*,7R*,8S*,9S*,10R*,12S*,13S*,14R*,15R*,16S*)>-5-Ethyl-2,2,3,3,6,8,10,12,14,16,20,20-dodecamethyl-19,19-diphenyl-7,9,13,15-tetrakis(phenylmethoxy)-4,18-dioxa-3,19-disilaheneicosane (Protected Hexaol 41) (123992-33-6)

Guidance literature:

With triethylamine; In dichloromethane; for 0.25h; Ambient temperature;

DOI:10.1021/jo00292a045

Reference yield:

(E,Z)-3-<(tert-butyldimethylsilyl)oxy>-1-methoxy-2-methyl-1,3-pentadiene (98703-75-4) → <5R-(5R*,6R*,7R*,8S*,9S*,10R*,12S*,13S*,14R*,15R*,16S*)>-5-Ethyl-2,2,3,3,6,8,10,12,14,16,20,20-dodecamethyl-19,19-diphenyl-7,9,13,15-tetrakis(phenylmethoxy)-4,18-dioxa-3,19-disilaheneicosane (Protected Hexaol 41) (123992-33-6)

Guidance literature:

Multi-step reaction with 17 steps

1: 40 percent / 1) BF₃ etherate, 2) pyridinium p-toluenesulfonate / CH₂Cl₂; benzene / 1) -78 deg C, 40 min, 2) reflux, 1h

2: 86 percent / cerium trichloride heptahydrate, NaBH₄ / ethanol / -15 °C

3: 91 percent / p-toluenesulfonic acid monohydrate / 2 h / Ambient temperature

4: 80 percent / H₂, 5percent Pd/Al / ethyl acetate / 36 h

5: 69 percent / TiCl₄ / CH₂Cl₂ / -78 °C

6: 94 percent / 95percent NaH, tetrabutylammonium iodide / tetrahydrofuran / 12 h / Heating

7: NBS / acetone; H₂O / -15 °C

8: 1) BF₃ etherate, 2) pyridinium p-toluenesulfonate / CH₂Cl₂; benzene / 1) -78 deg C, 45 min, 2) reflux, 2h

9: 92 percent / ceriumtrichloride heptahydrate, NaBH₄ / ethanol / -15 °C

10: 56 percent / 1) p-toluenesulfonic acid monohydrate, 2) LiBH₄ / tetrahydrofuran / 1) reflux, 45 min, 2) r.t., 2h

11: 82.3 percent / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 12 h / Ambient temperature

12: 88.5 percent / 1) trifluoromethanesulfonic acid, 2) LiAlH₄ / cyclohexane / 1) 12h, 2) 2h, r.t.

13: 87 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / Ambient temperature

14: trifluoromethanesulfonic acid / cyclohexane / 48 h

15: 31 percent / LiAlH₄ / diethyl ether / 1 h / Ambient temperature

16: 89 percent / 4-(dimethylamino)pyridine, Et₃N / 24 h

17: 96 percent / Et₃N / CH₂Cl₂ / 0.25 h / Ambient temperature

With dmap; sodium tetrahydroborate; N-Bromosuccinimide; lithium aluminium tetrahydride; lithium borohydride; cerium(III) chloride; trifluorormethanesulfonic acid; Pd/Al; boron trifluoride diethyl etherate; hydrogen; pyridinium p-toluenesulfonate; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; sodium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; cyclohexane; water; ethyl acetate; acetone; benzene;

DOI:10.1021/jo00292a045

Reference yield:

1,5-Anhydro-2,4,6,8-tetradeoxy-9-O-<(1,1-dimethylethyl)-diphenylsilyl>-2,4,6,8-tetramethyl-7-O-(phenylmethyl)-L-glycero-D-gulo-non-1-en-3-ulose (Pyrone 11) (123992-11-0) → <5R-(5R*,6R*,7R*,8S*,9S*,10R*,12S*,13S*,14R*,15R*,16S*)>-5-Ethyl-2,2,3,3,6,8,10,12,14,16,20,20-dodecamethyl-19,19-diphenyl-7,9,13,15-tetrakis(phenylmethoxy)-4,18-dioxa-3,19-disilaheneicosane (Protected Hexaol 41) (123992-33-6)

Guidance literature:

Multi-step reaction with 16 steps

1: 86 percent / cerium trichloride heptahydrate, NaBH₄ / ethanol / -15 °C

2: 91 percent / p-toluenesulfonic acid monohydrate / 2 h / Ambient temperature

3: 80 percent / H₂, 5percent Pd/Al / ethyl acetate / 36 h

4: 69 percent / TiCl₄ / CH₂Cl₂ / -78 °C

5: 94 percent / 95percent NaH, tetrabutylammonium iodide / tetrahydrofuran / 12 h / Heating

6: NBS / acetone; H₂O / -15 °C

7: 1) BF₃ etherate, 2) pyridinium p-toluenesulfonate / CH₂Cl₂; benzene / 1) -78 deg C, 45 min, 2) reflux, 2h

8: 92 percent / ceriumtrichloride heptahydrate, NaBH₄ / ethanol / -15 °C

9: 56 percent / 1) p-toluenesulfonic acid monohydrate, 2) LiBH₄ / tetrahydrofuran / 1) reflux, 45 min, 2) r.t., 2h

10: 82.3 percent / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 12 h / Ambient temperature

11: 88.5 percent / 1) trifluoromethanesulfonic acid, 2) LiAlH₄ / cyclohexane / 1) 12h, 2) 2h, r.t.

12: 87 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / Ambient temperature

13: trifluoromethanesulfonic acid / cyclohexane / 48 h

14: 31 percent / LiAlH₄ / diethyl ether / 1 h / Ambient temperature

15: 89 percent / 4-(dimethylamino)pyridine, Et₃N / 24 h

16: 96 percent / Et₃N / CH₂Cl₂ / 0.25 h / Ambient temperature

With dmap; sodium tetrahydroborate; N-Bromosuccinimide; lithium aluminium tetrahydride; lithium borohydride; cerium(III) chloride; trifluorormethanesulfonic acid; Pd/Al; boron trifluoride diethyl etherate; hydrogen; pyridinium p-toluenesulfonate; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; sodium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; cyclohexane; water; ethyl acetate; acetone; benzene;

DOI:10.1021/jo00292a045

upstream raw materials:

<3R-(3R*,4S*,5S*,6S*,8R*,10S*,11S*,12R*,13R*,14S*)>-153-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>-4,6,8,10,12,14-hexamethyl-5,7,11,13-tetrakis(phenylmethoxy)-3-pentadecanol (Alcohol 2)

tert-butyldimethylsilyl triflate

2,3-Dihydro-3,5-dimethyl-4H-pyran-4-one (Pyrone 4)

Methyl 2,4-Dideoxy-2,4-dimethyl-α-L-xylopyranoside (Pyran 6)