(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

Base Information

• Chemical Name: (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
• CAS No.: 864712-65-2
• Molecular Formula: C₅₉H₈₅NO₉Si₂
• Molecular Weight: 1008.5
• Mol file: 864712-65-2.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 32 articles about (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 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: 65.0%

(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 (864712-80-1) + N,N-Dimethylcarbamoyl chloride (79-44-7) → (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 (864712-65-2)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide;

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,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 (864712-65-2)

Guidance literature:

Multi-step reaction with 13 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

10.1: 237 mg / N-methylmorpholine N-oxide; tetrapropylammonium perruthenate / CH₂Cl₂ / 1.5 h / 20 °C

11.1: 250 mg / benzene / 12 h / 100 °C

12.1: 95 percent / DDQ / CH₂Cl₂; H₂O / 0.83 h / 0 °C

13.1: 64 percent / NaH / dimethylformamide; various solvent(s) / 1 h / 0 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; lithium borohydride; tetrapropylammonium perruthennate; diethyl (2S,3S)-tartrate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; pyridinium p-toluenesulfonate; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene; 6.1: Dess Martin oxidation / 7.1: Wittig reaction / 9.1: Miyashita epoxidation;

DOI:10.1246/bcsj.79.468

Reference yield:

(E,4S,5R,6R)-methyl 4,5-bis(benzyloxy)-12-t-butyldiphenylsiloxy-6-triethylsiloxy-6-methyldodec-2-enoate (887768-95-8) → (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 (864712-65-2)

Guidance literature:

Multi-step reaction with 16 steps

1: 100 percent / N-methylmorpholine N-oxide / OsO₄ / acetone; H₂O; 2-methyl-propan-2-ol / 40 h / 0 - 20 °C

2: 100 percent / LiBH₄ / tetrahydrofuran / 2 h / 0 °C

3: 81 percent / benzene / 1.5 h / 20 °C

4: 515 mg / 4-(dimethylamino)pyridine / pyridine / 12 h / 20 °C

5: 424 mg / NaOMe / methanol; tetrahydrofuran / 4 h / 0 °C

6: 87 percent / CuCN / diethyl ether / 8 h / 0 °C

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

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

9: 98.1 mg / Dess Martin periodinane; NaHCO₃ / CH₂Cl₂ / 4 h / 20 °C

10: 101 mg / benzene / 18 h / 100 °C

11: 100 percent / LiBH₄ / tetrahydrofuran / 3.5 h / 20 °C

12: 75 percent / mCPBA; NaHCO₃ / CH₂Cl₂ / 1 h / -22 °C

13: 237 mg / N-methylmorpholine N-oxide; tetrapropylammonium perruthenate / CH₂Cl₂ / 1.5 h / 20 °C

14: 250 mg / benzene / 12 h / 100 °C

15: 95 percent / DDQ / CH₂Cl₂; H₂O / 0.83 h / 0 °C

16: 64 percent / NaH / dimethylformamide; various solvent(s) / 1 h / 0 °C

With dmap; lithium borohydride; tetrapropylammonium perruthennate; sodium methylate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; osmium(VIII) oxide; pyridinium p-toluenesulfonate; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; benzene; 9: Dess Martin oxidation / 10: Wittig reaction / 12: Miyashita epoxidation;

DOI:10.1246/bcsj.79.468

upstream raw materials:

(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

N,N-Dimethylcarbamoyl chloride

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