2,2-Dimethyl-propionic acid (R)-4-[(1S,3R,4R,5R,6R,7R)-4-benzyloxy-3,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-6,7-dihydroxy-2,8-dioxa-bicyclo[3.2.1]oct-1-yl]-1-((R)-1-methyl-2-phenyl-ethyl)-butyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (R)-4-[(1S,3R,4R,5R,6R,7R)-4-benzyloxy-3,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-6,7-dihydroxy-2,8-dioxa-bicyclo[3.2.1]oct-1-yl]-1-((R)-1-methyl-2-phenyl-ethyl)-butyl ester
• CAS No.: 164215-37-6
• Molecular Formula: C₄₅H₇₄O₉Si₂
• Molecular Weight: 815.248

Synonyms:2,2-Dimethyl-propionic acid (R)-4-[(1S,3R,4R,5R,6R,7R)-4-benzyloxy-3,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-6,7-dihydroxy-2,8-dioxa-bicyclo[3.2.1]oct-1-yl]-1-((R)-1-methyl-2-phenyl-ethyl)-butyl ester

Chemical Property of 2,2-Dimethyl-propionic acid (R)-4-[(1S,3R,4R,5R,6R,7R)-4-benzyloxy-3,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-6,7-dihydroxy-2,8-dioxa-bicyclo[3.2.1]oct-1-yl]-1-((R)-1-methyl-2-phenyl-ethyl)-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid (R)-4-[(1S,3R,4R,5R,6R,7R)-4-benzyloxy-3,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-6,7-dihydroxy-2,8-dioxa-bicyclo[3.2.1]oct-1-yl]-1-((R)-1-methyl-2-phenyl-ethyl)-butyl ester

There total 25 articles about 2,2-Dimethyl-propionic acid (R)-4-[(1S,3R,4R,5R,6R,7R)-4-benzyloxy-3,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-6,7-dihydroxy-2,8-dioxa-bicyclo[3.2.1]oct-1-yl]-1-((R)-1-methyl-2-phenyl-ethyl)-butyl ester 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:

5-benzyloxy-1-pentanal (78999-24-3) → 2,2-Dimethyl-propionic acid (R)-4-[(1S,3R,4R,5R,6R,7R)-4-benzyloxy-3,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-6,7-dihydroxy-2,8-dioxa-bicyclo[3.2.1]oct-1-yl]-1-((R)-1-methyl-2-phenyl-ethyl)-butyl ester (164215-37-6)

Guidance literature:

Multi-step reaction with 16 steps

1: 1.) 9-BBNOTf, i-Pr₂NEt / 1.) CH₂Cl₂, a) -78 deg C, 30 min, b) 0 deg C, 3 h, 2.) CH₂Cl₂, 23 deg C, 12 h

2: 17.5 g / aq. LiOH, 30percent aq. H₂O₂ / tetrahydrofuran / 3 h / 0 °C

3: 92 percent / LiAlH₄ / tetrahydrofuran / 8 h / Heating

4: 89 percent / pyridine / 42 h / 0 °C

5: PhLi / cyclohexane; diethyl ether / 0.5 h / 23 °C

6: BF₃*OEt₂ / cyclohexane; diethyl ether / 1 h / -78 - 0 °C

7: 90 percent / 4-DMAP / CH₂Cl₂ / 16 h / Heating

8: 99 percent / H₂ / 5percent Pd/C / ethyl acetate / 12 h / 23 °C / 760 Torr

9: 1.) DMSO, oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) CH₂Cl₂, from -78 to 0 deg C

10: 1.) n-BuLi, 2.) LiBr / 1.) THF, hexane, -45 deg C, 45 min, 2.) THF, hexane, -45 deg C, 10 min

11: 93 percent / Dess-Martin periodinane / CH₂Cl₂ / 5 h / 23 °C

12: 60 percent / 2O>2 / H₂O; tetrahydrofuran / 336 h / 65 °C

13: 93 percent / n-Bu₄NF / tetrahydrofuran / 0.75 h

14: (DHQD)2PHAL, 4-methylmorpholine N-oxide, CH₃SO₂NH₂, aq. OsO₄ / acetone; 2-methyl-propan-2-ol / 12 h / 23 °C

15: 86 percent / 12N aq. HCl / methanol / 2 h / 23 °C

16: Et₃N, 4-DMAP / CH₂Cl₂ / 46 h / 23 °C

With pyridine; hydrogenchloride; dmap; lithium hydroxide; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; methanesulfonamide; 2; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; Dess-Martin periodane; dimethyl sulfoxide; phenyllithium; 4-methylmorpholine N-oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; N-ethyl-N,N-diisopropylamine; lithium bromide; 9-BBN triflate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; cyclohexane; water; ethyl acetate; acetone; tert-butyl alcohol;

DOI:10.1021/ja00136a008

Reference yield:

(2R,3R)-2-(4-Benzyloxy-butyl)-3-methyl-oxetane → 2,2-Dimethyl-propionic acid (R)-4-[(1S,3R,4R,5R,6R,7R)-4-benzyloxy-3,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-6,7-dihydroxy-2,8-dioxa-bicyclo[3.2.1]oct-1-yl]-1-((R)-1-methyl-2-phenyl-ethyl)-butyl ester (164215-37-6)

Guidance literature:

Multi-step reaction with 11 steps

1: BF₃*OEt₂ / cyclohexane; diethyl ether / 1 h / -78 - 0 °C

2: 90 percent / 4-DMAP / CH₂Cl₂ / 16 h / Heating

3: 99 percent / H₂ / 5percent Pd/C / ethyl acetate / 12 h / 23 °C / 760 Torr

4: 1.) DMSO, oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) CH₂Cl₂, from -78 to 0 deg C

5: 1.) n-BuLi, 2.) LiBr / 1.) THF, hexane, -45 deg C, 45 min, 2.) THF, hexane, -45 deg C, 10 min

6: 93 percent / Dess-Martin periodinane / CH₂Cl₂ / 5 h / 23 °C

7: 60 percent / 2O>2 / H₂O; tetrahydrofuran / 336 h / 65 °C

8: 93 percent / n-Bu₄NF / tetrahydrofuran / 0.75 h

9: (DHQD)2PHAL, 4-methylmorpholine N-oxide, CH₃SO₂NH₂, aq. OsO₄ / acetone; 2-methyl-propan-2-ol / 12 h / 23 °C

10: 86 percent / 12N aq. HCl / methanol / 2 h / 23 °C

11: Et₃N, 4-DMAP / CH₂Cl₂ / 46 h / 23 °C

With hydrogenchloride; dmap; osmium(VIII) oxide; n-butyllithium; oxalyl dichloride; methanesulfonamide; 2; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; Dess-Martin periodane; dimethyl sulfoxide; 4-methylmorpholine N-oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; lithium bromide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; cyclohexane; water; ethyl acetate; acetone; tert-butyl alcohol;

DOI:10.1021/ja00136a008

Reference yield:

(2R,3R)-7-Benzyloxy-2-methyl-heptane-1,3-diol (171189-81-4) → 2,2-Dimethyl-propionic acid (R)-4-[(1S,3R,4R,5R,6R,7R)-4-benzyloxy-3,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-6,7-dihydroxy-2,8-dioxa-bicyclo[3.2.1]oct-1-yl]-1-((R)-1-methyl-2-phenyl-ethyl)-butyl ester (164215-37-6)

Guidance literature:

Multi-step reaction with 13 steps

1: 89 percent / pyridine / 42 h / 0 °C

2: PhLi / cyclohexane; diethyl ether / 0.5 h / 23 °C

3: BF₃*OEt₂ / cyclohexane; diethyl ether / 1 h / -78 - 0 °C

4: 90 percent / 4-DMAP / CH₂Cl₂ / 16 h / Heating

5: 99 percent / H₂ / 5percent Pd/C / ethyl acetate / 12 h / 23 °C / 760 Torr

6: 1.) DMSO, oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) CH₂Cl₂, from -78 to 0 deg C

7: 1.) n-BuLi, 2.) LiBr / 1.) THF, hexane, -45 deg C, 45 min, 2.) THF, hexane, -45 deg C, 10 min

8: 93 percent / Dess-Martin periodinane / CH₂Cl₂ / 5 h / 23 °C

9: 60 percent / 2O>2 / H₂O; tetrahydrofuran / 336 h / 65 °C

10: 93 percent / n-Bu₄NF / tetrahydrofuran / 0.75 h

11: (DHQD)2PHAL, 4-methylmorpholine N-oxide, CH₃SO₂NH₂, aq. OsO₄ / acetone; 2-methyl-propan-2-ol / 12 h / 23 °C

12: 86 percent / 12N aq. HCl / methanol / 2 h / 23 °C

13: Et₃N, 4-DMAP / CH₂Cl₂ / 46 h / 23 °C

With pyridine; hydrogenchloride; dmap; osmium(VIII) oxide; n-butyllithium; oxalyl dichloride; methanesulfonamide; 2; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; Dess-Martin periodane; dimethyl sulfoxide; phenyllithium; 4-methylmorpholine N-oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; lithium bromide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; cyclohexane; water; ethyl acetate; acetone; tert-butyl alcohol;

DOI:10.1021/ja00136a008

upstream raw materials:

tert-butyldimethylsilyl chloride

2,2-Dimethyl-propionic acid (E)-(1R,8S,9R)-9-benzyloxy-9-((R)-2,2-diethyl-[1,3]dioxolan-4-yl)-8-hydroxy-8-hydroxymethyl-1-((R)-1-methyl-2-phenyl-ethyl)-5-oxo-non-6-enyl ester

5-benzyloxy-1-pentanal

2,2-Dimethyl-propionic acid (R)-1-((R)-1-methyl-2-phenyl-ethyl)-5-oxo-pentyl ester

Downstream raw materials:

2,2-Dimethyl-propionic acid (1S,3R,4R,5S,6R,7R)-4-benzyloxy-3,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-7-(2,2-dimethyl-propionyloxy)-1-[(4R,5R)-4-(2,2-dimethyl-propionyloxy)-5-methyl-6-phenyl-hexyl]-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester

2,2-Dimethyl-propionic acid (1S,3R,4R,5S,6R,7R)-3,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-7-(2,2-dimethyl-propionyloxy)-1-[(4R,5R)-4-(2,2-dimethyl-propionyloxy)-5-methyl-6-phenyl-hexyl]-4-hydroxy-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester

2,2-Dimethyl-propionic acid (1S,3R,5R,6R,7R)-3,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-7-(2,2-dimethyl-propionyloxy)-1-[(4R,5R)-4-(2,2-dimethyl-propionyloxy)-5-methyl-6-phenyl-hexyl]-4-oxo-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester

2,2-Dimethyl-propionic acid (1S,3R,4S,5R,6R,7R)-3,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-7-(2,2-dimethyl-propionyloxy)-1-[(4R,5R)-4-(2,2-dimethyl-propionyloxy)-5-methyl-6-phenyl-hexyl]-4-ethynyl-4-hydroxy-2,8-dioxa-bicyclo[3.2.1]oct-6-yl ester

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 164215-37-6 2,2-Dimethyl-propionic acid (R)-4-[(1S,3R,4R,5R,6R,7R)-4-benzyloxy-3,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-6,7-dihydroxy-2,8-dioxa-bicyclo[3.2.1]oct-1-yl]-1-((R)-1-methyl-2-phenyl-ethyl)-butyl ester

Send

Send

Metric Ton KG G Pound L ML

Send

Send