{(2R,3R)-3-[(2R,3R,4S,5R,6R)-4,5-bis(benzyloxy)-12-t-butyldiphenylsiloxy-6-triethylsiloxy-3-(4-methoxybenzyloxy)-6-methyldodecan-2-yl]-2-methyloxiran-2-yl}methanol

Base Information

• Chemical Name: {(2R,3R)-3-[(2R,3R,4S,5R,6R)-4,5-bis(benzyloxy)-12-t-butyldiphenylsiloxy-6-triethylsiloxy-3-(4-methoxybenzyloxy)-6-methyldodecan-2-yl]-2-methyloxiran-2-yl}methanol
• CAS No.: 864712-79-8
• Molecular Formula: C₆₁H₈₆O₈Si₂
• Molecular Weight: 1003.52
• Mol file: 864712-79-8.mol

Synonyms:{(2R,3R)-3-[(2R,3R,4S,5R,6R)-4,5-bis(benzyloxy)-12-t-butyldiphenylsiloxy-6-triethylsiloxy-3-(4-methoxybenzyloxy)-6-methyldodecan-2-yl]-2-methyloxiran-2-yl}methanol

Chemical Property of {(2R,3R)-3-[(2R,3R,4S,5R,6R)-4,5-bis(benzyloxy)-12-t-butyldiphenylsiloxy-6-triethylsiloxy-3-(4-methoxybenzyloxy)-6-methyldodecan-2-yl]-2-methyloxiran-2-yl}methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(2R,3R)-3-[(2R,3R,4S,5R,6R)-4,5-bis(benzyloxy)-12-t-butyldiphenylsiloxy-6-triethylsiloxy-3-(4-methoxybenzyloxy)-6-methyldodecan-2-yl]-2-methyloxiran-2-yl}methanol

There total 28 articles about {(2R,3R)-3-[(2R,3R,4S,5R,6R)-4,5-bis(benzyloxy)-12-t-butyldiphenylsiloxy-6-triethylsiloxy-3-(4-methoxybenzyloxy)-6-methyldodecan-2-yl]-2-methyloxiran-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: 75.0%

(E,4S,5R,6S,7R,8R)-6,7-bis(benzyloxy)-14-t-butyldiphenylsiloxy-8-triethylsiloxy-5-(4-methoxybenzyloxy)-2,4,8-trimethyltetradec-2-en-1-ol (887768-94-7) → {(2R,3R)-3-[(2R,3R,4S,5R,6R)-4,5-bis(benzyloxy)-12-t-butyldiphenylsiloxy-6-triethylsiloxy-3-(4-methoxybenzyloxy)-6-methyldodecan-2-yl]-2-methyloxiran-2-yl}methanol (864712-79-8)

Guidance literature:

With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -22 ℃; for 1h;

DOI:10.1246/bcsj.79.468

Reference yield: 70.0%

(E,4S,5R,6S,7R,8R)-methyl 6,7-bis(benzyloxy)-14-t-butyldiphenylsiloxy-8-triethylsiloxy-5-(4-methoxybenzyloxy)-2,4,8-trimethyltetradec-2-enoate (864712-74-3) → {(2R,3R)-3-[(2R,3R,4S,5R,6R)-4,5-bis(benzyloxy)-12-t-butyldiphenylsiloxy-6-triethylsiloxy-3-(4-methoxybenzyloxy)-6-methyldodecan-2-yl]-2-methyloxiran-2-yl}methanol (864712-79-8)

Guidance literature:

(E,4S,5R,6S,7R,8R)-methyl 6,7-bis(benzyloxy)-14-t-butyldiphenylsiloxy-8-triethylsiloxy-5-(4-methoxybenzyloxy)-2,4,8-trimethyltetradec-2-enoate; With lithium borohydride; In tetrahydrofuran;

With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1016/j.tetlet.2005.06.079

Reference yield:

(2R,3R,4R)-2,3-bis(benzyloxy)-10-t-butyldiphenylsiloxy-4-triethylsiloxy-4-methyldecanal (864712-67-4) → {(2R,3R)-3-[(2R,3R,4S,5R,6R)-4,5-bis(benzyloxy)-12-t-butyldiphenylsiloxy-6-triethylsiloxy-3-(4-methoxybenzyloxy)-6-methyldodecan-2-yl]-2-methyloxiran-2-yl}methanol (864712-79-8)

Guidance literature:

Multi-step reaction with 9 steps

1.1: NaH / tetrahydrofuran

1.2: DIBAL-H / CH₂Cl₂; tetrahydrofuran

2.1: 20 percent / Ti(O-iPr)4; D-(-)-DET; t-butylhydroperoxide / CH₂Cl₂

3.1: 87 percent / CuCN / diethyl ether / 8 h / 0 °C

4.1: 100 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 7 h / 20 °C

5.1: 64 percent / DIBAL-H / toluene / 8 h / 0 °C

6.1: 98.1 mg / Dess Martin periodinane; NaHCO₃ / CH₂Cl₂ / 4 h / 20 °C

7.1: 101 mg / benzene / 18 h / 100 °C

8.1: 100 percent / LiBH₄ / tetrahydrofuran / 3.5 h / 20 °C

9.1: 75 percent / mCPBA; NaHCO₃ / CH₂Cl₂ / 1 h / -22 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; lithium borohydride; diethyl (2S,3S)-tartrate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; pyridinium p-toluenesulfonate; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; benzene; 6.1: Dess Martin oxidation / 7.1: Wittig reaction / 9.1: Miyashita epoxidation;

DOI:10.1246/bcsj.79.468

upstream raw materials:

(E,4S,5R,6S,7R,8R)-methyl 6,7-bis(benzyloxy)-14-t-butyldiphenylsiloxy-8-triethylsiloxy-5-(4-methoxybenzyloxy)-2,4,8-trimethyltetradec-2-enoate

(E,4S,5R,6S,7R,8R)-6,7-bis(benzyloxy)-14-t-butyldiphenylsiloxy-8-triethylsiloxy-5-(4-methoxybenzyloxy)-2,4,8-trimethyltetradec-2-en-1-ol

3,4-bis(benzyloxy)tetrahydro-5-methoxy-2-methyl-2-vinylfuran

((2R,3R,4R)-3,4-Bis-benzyloxy-5-methoxy-2-methyl-tetrahydro-furan-2-yl)-acetaldehyde

Downstream raw materials:

(2S,3R)-3-[(1R,2R,3S,4R,5R)-3,4-Bis-benzyloxy-11-(tert-butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxy)-1,5-dimethyl-5-triethylsilanyloxy-undecyl]-2-methyl-oxirane-2-carbaldehyde

(E)-3-{(2R,3R)-3-[(1R,2R,3S,4R,5R)-3,4-Bis-benzyloxy-11-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-1,5-dimethyl-5-triethylsilanyloxy-undecyl]-2-methyl-oxiranyl}-acrylic acid methyl ester

(2R,3R,4S,5R,6R)-2-{(2R,3R)-3-[(E)-2-(methoxycarbonyl)vinyl]-3-methyloxiran-2-yl}-4,5-bis(benzyloxy)-12-t-butyldiphenylsiloxy-6-triethylsiloxy-6-methyldodecan-3-yl dimethylcarbamate

(E)-methyl 3-{(2R,3R)-3-[(2R,3R,4S,5R,6R)-4,5-bis(benzyloxy)-12-t-butyldiphenylsiloxy-6-triethylsiloxy-3-(4-methoxybenzyloxy)-6-methyldodecan-2-yl]-2-methyloxiran-2-yl}acrylate