(R)-2-Benzyloxy-1-{6-[(2R,4R,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-1,5,9,10-tetramethoxy-anthracen-2-yl}-2-methyl-pent-4-en-1-ol

Base Information

• Chemical Name: (R)-2-Benzyloxy-1-{6-[(2R,4R,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-1,5,9,10-tetramethoxy-anthracen-2-yl}-2-methyl-pent-4-en-1-ol
• CAS No.: 136459-97-7
• Molecular Formula: C₄₉H₇₂O₉Si₂
• Molecular Weight: 861.276
• Mol file: 136459-97-7.mol

Synonyms:

Chemical Property of (R)-2-Benzyloxy-1-{6-[(2R,4R,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-1,5,9,10-tetramethoxy-anthracen-2-yl}-2-methyl-pent-4-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-Benzyloxy-1-{6-[(2R,4R,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-1,5,9,10-tetramethoxy-anthracen-2-yl}-2-methyl-pent-4-en-1-ol

There total 26 articles about (R)-2-Benzyloxy-1-{6-[(2R,4R,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-1,5,9,10-tetramethoxy-anthracen-2-yl}-2-methyl-pent-4-en-1-ol 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:

1-hydroxy-5-methoxy-9,10-anthraquinone (52869-21-3) → (S)-2-Benzyloxy-1-{6-[(2R,4R,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-1,5,9,10-tetramethoxy-anthracen-2-yl}-2-methyl-pent-4-en-1-ol (136459-97-7,136521-76-1,136521-80-7,136521-81-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 100 percent / (i-Pr)2NEt / CH₂Cl₂ / Ambient temperature

2: H₂ / 10percent Pd/C / dimethylformamide / 0.25 h / 760 Torr / Ambient temperature

3: 1.) NaH / 1.) DMF, RT, 15 min, 2.) DMF, RT, 20 min

4: 92.3 percent / EtSH, BF₃*OEt₂ / CH₂Cl₂ / 1.) -78 deg C, 20 min, 2.) from -78 deg C to -20 deg C , 30 min

5: 85.5 percent / Cp₂HfCl₂, AgClO₄, molecular sieves 4A / CH₂Cl₂ / 0.83 h / -78 - 0 °C

6: 100 percent / NaH / tetrahydrofuran / 2 h / Ambient temperature

7: 96.2 percent / 3 N aq. NaOH / methanol / Ambient temperature

8: 96.4 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / Ambient temperature

With 2,6-dimethylpyridine; sodium hydroxide; bis(cyclopentadienyl)hafnium dichloride; 4 A molecular sieve; boron trifluoride diethyl etherate; hydrogen; silver perchlorate; sodium hydride; N-ethyl-N,N-diisopropylamine; ethanethiol; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00018a041

Reference yield:

1-hydroxy-5-methoxy-9,10-anthraquinone (52869-21-3) → (R)-2-Benzyloxy-1-{6-[(2R,4R,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-1,5,9,10-tetramethoxy-anthracen-2-yl}-2-methyl-pent-4-en-1-ol (136459-97-7,136521-76-1,136521-80-7,136521-81-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 100 percent / (i-Pr)2NEt / CH₂Cl₂ / Ambient temperature

2: H₂ / 10percent Pd/C / dimethylformamide / 0.25 h / 760 Torr / Ambient temperature

3: 1.) NaH / 1.) DMF, RT, 15 min, 2.) DMF, RT, 20 min

4: 92.3 percent / EtSH, BF₃*OEt₂ / CH₂Cl₂ / 1.) -78 deg C, 20 min, 2.) from -78 deg C to -20 deg C , 30 min

5: 85.5 percent / Cp₂HfCl₂, AgClO₄, molecular sieves 4A / CH₂Cl₂ / 0.83 h / -78 - 0 °C

6: 100 percent / NaH / tetrahydrofuran / 2 h / Ambient temperature

7: 96.2 percent / 3 N aq. NaOH / methanol / Ambient temperature

8: 96.4 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / Ambient temperature

With 2,6-dimethylpyridine; sodium hydroxide; bis(cyclopentadienyl)hafnium dichloride; 4 A molecular sieve; boron trifluoride diethyl etherate; hydrogen; silver perchlorate; sodium hydride; N-ethyl-N,N-diisopropylamine; ethanethiol; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00018a041

Reference yield:

1-(methoxymethoxy)-5-methoxy-9,10-anthraquinone (121564-53-2) → (S)-2-Benzyloxy-1-{6-[(2R,4R,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-1,5,9,10-tetramethoxy-anthracen-2-yl}-2-methyl-pent-4-en-1-ol (136459-97-7,136521-76-1,136521-80-7,136521-81-8)

Guidance literature:

Multi-step reaction with 8 steps

1: H₂ / 10percent Pd/C / dimethylformamide / 0.25 h / 760 Torr / Ambient temperature

2: 1.) NaH / 1.) DMF, RT, 15 min, 2.) DMF, RT, 20 min

3: 92.3 percent / EtSH, BF₃*OEt₂ / CH₂Cl₂ / 1.) -78 deg C, 20 min, 2.) from -78 deg C to -20 deg C , 30 min

4: 85.5 percent / Cp₂HfCl₂, AgClO₄, molecular sieves 4A / CH₂Cl₂ / 0.83 h / -78 - 0 °C

5: 100 percent / NaH / tetrahydrofuran / 2 h / Ambient temperature

6: 96.2 percent / 3 N aq. NaOH / methanol / Ambient temperature

7: 96.4 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / Ambient temperature

With 2,6-dimethylpyridine; sodium hydroxide; bis(cyclopentadienyl)hafnium dichloride; 4 A molecular sieve; boron trifluoride diethyl etherate; hydrogen; silver perchlorate; sodium hydride; ethanethiol; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00018a041

upstream raw materials:

(2R,3R,4R,6R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-(1,5,9,10-tetramethoxy-anthracen-2-yl)-tetrahydro-pyran

(S)-2-Benzyloxy-2-methyl-pent-4-enal

1-hydroxy-5-methoxy-9,10-anthraquinone

t-butyldimethylsiyl triflate

Downstream raw materials:

Benzoic acid (R)-2-benzyloxy-1-{6-[(2R,4R,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-1,5-dimethoxy-9,10-dioxo-9,10-dihydro-anthracen-2-yl}-2-methyl-pent-4-enyl ester

Benzoic acid (R)-1-{6-[(2R,4R,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-1,5-dimethoxy-9,10-dioxo-9,10-dihydro-anthracen-2-yl}-2-hydroxy-2-methyl-pent-4-enyl ester

Benzoic acid (R)-2-benzyloxy-1-{6-[(2R,4R,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-1,5,9,10-tetramethoxy-anthracen-2-yl}-2-methyl-pent-4-enyl ester

Benzoic acid (S)-2-benzyloxy-1-{6-[(2R,4R,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-1,5-dimethoxy-9,10-dioxo-9,10-dihydro-anthracen-2-yl}-2-methyl-pent-4-enyl ester