(2R,4S,5S,6R)-4-(t-butyldimethylsiloxy)-6-(4-chlorobutyl)-2-methoxy-2-[[4,5-(R,R)-bis-(p-methoxybenzyloxy)-3-(R)-methyl-6-(R)-(2-methylallyl)-tetrahydropyran-2-(R)-yl]-((S)-p-methoxybenzyloxy)-methyl]-5-methyl-tetrahydropyran

Base Information

• Chemical Name: (2R,4S,5S,6R)-4-(t-butyldimethylsiloxy)-6-(4-chlorobutyl)-2-methoxy-2-[[4,5-(R,R)-bis-(p-methoxybenzyloxy)-3-(R)-methyl-6-(R)-(2-methylallyl)-tetrahydropyran-2-(R)-yl]-((S)-p-methoxybenzyloxy)-methyl]-5-methyl-tetrahydropyran
• CAS No.: 537041-15-9
• Molecular Formula: C₅₂H₇₇ClO₁₀Si
• Molecular Weight: 925.716

Synonyms:(2R,4S,5S,6R)-4-(t-butyldimethylsiloxy)-6-(4-chlorobutyl)-2-methoxy-2-[[4,5-(R,R)-bis-(p-methoxybenzyloxy)-3-(R)-methyl-6-(R)-(2-methylallyl)-tetrahydropyran-2-(R)-yl]-((S)-p-methoxybenzyloxy)-methyl]-5-methyl-tetrahydropyran

Chemical Property of (2R,4S,5S,6R)-4-(t-butyldimethylsiloxy)-6-(4-chlorobutyl)-2-methoxy-2-[[4,5-(R,R)-bis-(p-methoxybenzyloxy)-3-(R)-methyl-6-(R)-(2-methylallyl)-tetrahydropyran-2-(R)-yl]-((S)-p-methoxybenzyloxy)-methyl]-5-methyl-tetrahydropyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4S,5S,6R)-4-(t-butyldimethylsiloxy)-6-(4-chlorobutyl)-2-methoxy-2-[[4,5-(R,R)-bis-(p-methoxybenzyloxy)-3-(R)-methyl-6-(R)-(2-methylallyl)-tetrahydropyran-2-(R)-yl]-((S)-p-methoxybenzyloxy)-methyl]-5-methyl-tetrahydropyran

There total 22 articles about (2R,4S,5S,6R)-4-(t-butyldimethylsiloxy)-6-(4-chlorobutyl)-2-methoxy-2-[[4,5-(R,R)-bis-(p-methoxybenzyloxy)-3-(R)-methyl-6-(R)-(2-methylallyl)-tetrahydropyran-2-(R)-yl]-((S)-p-methoxybenzyloxy)-methyl]-5-methyl-tetrahydropyran 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: 98.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (2R,4S,5R,6R)-6-(4-chlorobutyl)-2-methoxy-2-[[4,5-(R,R)-bis-(p-methoxybenzyloxy)-3-(R)-methyl-6-(R)-(2-methylallyl)-tetrahydropyran-2-(R)-yl]-((S)-p-methoxybenzyloxy)-methyl]-5-methyl-tetrahydropyran-4-ol (392692-63-6) → (2R,4S,5S,6R)-4-(t-butyldimethylsiloxy)-6-(4-chlorobutyl)-2-methoxy-2-[[4,5-(R,R)-bis-(p-methoxybenzyloxy)-3-(R)-methyl-6-(R)-(2-methylallyl)-tetrahydropyran-2-(R)-yl]-((S)-p-methoxybenzyloxy)-methyl]-5-methyl-tetrahydropyran (537041-15-9)

Guidance literature:

With 1H-imidazole; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 48h;

DOI:10.1039/b504149j

Reference yield:

(4R,5R,6R)-5-benzyloxy-4-[1-hydroxy-prop-2-(R)-yl]-2,2,6-trimethyl-1,3-dioxane (862509-84-0) → (2R,4S,5S,6R)-4-(t-butyldimethylsiloxy)-6-(4-chlorobutyl)-2-methoxy-2-[[4,5-(R,R)-bis-(p-methoxybenzyloxy)-3-(R)-methyl-6-(R)-(2-methylallyl)-tetrahydropyran-2-(R)-yl]-((S)-p-methoxybenzyloxy)-methyl]-5-methyl-tetrahydropyran (537041-15-9)

Guidance literature:

Multi-step reaction with 13 steps

1.1: Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

2.1: LiCl; i-PrNEt₂ / acetonitrile / 16 h / 20 °C

3.1: enriched AD-mix-β; MeSO3NH2 / 2-methyl-propan-2-ol; H2O / 8 h / 20 °C

4.1: H₂; NaHCO₃ / Pd(OH)2/C / methanol / 20 h / 20 °C

5.1: Ph₃CBF₄ / tetrahydrofuran / 2 h / 0 °C

6.1: DIBAL-H / CH₂Cl₂ / 0.5 h / -78 °C

6.2: Ba(OH)2 / tetrahydrofuran; H₂O / 16 h / 20 °C

7.1: AcOH / tetrahydrofuran; H₂O / 48 h / 20 °C

7.2: 86 percent / KOH / methanol / 24 h / 20 °C

8.1: toluene / 2 h / 120 °C

9.1: tetrapropylammonium perruthenate; N-methylmorpholine N-oxide / CH₂Cl₂ / 0.5 h / 20 °C

10.1: Et₃N / diethyl ether / 2.5 h / -78 °C

11.1: diethyl ether / 16 h / -78 - -20 °C

11.2: H₂O₂ / methanol; H₂O / 2 h / 0 - 20 °C / pH 7

12.1: PPTS / methanol / 1 h / 20 °C

13.1: imidazole; Et₃N / dimethylformamide / 16 h / 20 °C

With 1H-imidazole; tetrapropylammonium perruthennate; sulfamic acid methyl ester; N,N-diethyl-N-isopropylamine; enriched AD-mix-β; hydrogen; trityl tetrafluoroborate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; 4-methylmorpholine N-oxide; triethylamine; lithium chloride; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; 1.1: Dess-Martin oxidation / 2.1: Horner-Wadsworth-Emmons olefination / 3.1: Sharpless dihydroxylation / 6.2: Horner-Wadsworth-Emmons olefination / 7.1: hetero-Michael cyclization / 8.1: Petasis methylenation;

DOI:10.1002/1521-3773(20011105)40:21<4055::AID-ANIE4055>3.0.CO;2-H

Reference yield:

(R)-1-Benzyloxy-4-(4-methoxy-benzyloxy)-3-methyl-butan-2-one → (2R,4S,5S,6R)-4-(t-butyldimethylsiloxy)-6-(4-chlorobutyl)-2-methoxy-2-[[4,5-(R,R)-bis-(p-methoxybenzyloxy)-3-(R)-methyl-6-(R)-(2-methylallyl)-tetrahydropyran-2-(R)-yl]-((S)-p-methoxybenzyloxy)-methyl]-5-methyl-tetrahydropyran (537041-15-9)

Guidance literature:

Multi-step reaction with 17 steps

1.1: cHex₂BCl; Et₃N / diethyl ether / 2 h / -78 °C

1.2: 16 h / -78 - -20 °C

1.3: 93 percent / H₂O₂ / methanol; H₂O / 3 h / 0 - 20 °C / pH 7

2.1: Me₄NBH(OAc)3 / acetonitrile; acetic acid / 60 h / 4 °C

3.1: PPTS / CH₂Cl₂ / 16 h / 20 °C

4.1: DDQ / CH₂Cl₂ / 1.5 h / 0 °C / pH 7

5.1: Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

6.1: LiCl; i-PrNEt₂ / acetonitrile / 16 h / 20 °C

7.1: enriched AD-mix-β; MeSO3NH2 / 2-methyl-propan-2-ol; H2O / 8 h / 20 °C

8.1: H₂; NaHCO₃ / Pd(OH)2/C / methanol / 20 h / 20 °C

9.1: Ph₃CBF₄ / tetrahydrofuran / 2 h / 0 °C

10.1: DIBAL-H / CH₂Cl₂ / 0.5 h / -78 °C

10.2: Ba(OH)2 / tetrahydrofuran; H₂O / 16 h / 20 °C

11.1: AcOH / tetrahydrofuran; H₂O / 48 h / 20 °C

11.2: 86 percent / KOH / methanol / 24 h / 20 °C

12.1: toluene / 2 h / 120 °C

13.1: tetrapropylammonium perruthenate; N-methylmorpholine N-oxide / CH₂Cl₂ / 0.5 h / 20 °C

14.1: Et₃N / diethyl ether / 2.5 h / -78 °C

15.1: diethyl ether / 16 h / -78 - -20 °C

15.2: H₂O₂ / methanol; H₂O / 2 h / 0 - 20 °C / pH 7

16.1: PPTS / methanol / 1 h / 20 °C

17.1: imidazole; Et₃N / dimethylformamide / 16 h / 20 °C

With 1H-imidazole; tetrapropylammonium perruthennate; sulfamic acid methyl ester; N,N-diethyl-N-isopropylamine; enriched AD-mix-β; dicyclohexylboron chloride; hydrogen; trityl tetrafluoroborate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; 4-methylmorpholine N-oxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; tetramethylammonium triacetoxyborohydride; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; 5.1: Dess-Martin oxidation / 6.1: Horner-Wadsworth-Emmons olefination / 7.1: Sharpless dihydroxylation / 10.2: Horner-Wadsworth-Emmons olefination / 11.1: hetero-Michael cyclization / 12.1: Petasis methylenation;

DOI:10.1002/1521-3773(20011105)40:21<4055::AID-ANIE4055>3.0.CO;2-H

upstream raw materials:

tert-butyldimethylsilyl chloride

(2R,4S,5R,6R)-6-(4-chlorobutyl)-2-methoxy-2-[[4,5-(R,R)-bis-(p-methoxybenzyloxy)-3-(R)-methyl-6-(R)-(2-methylallyl)-tetrahydropyran-2-(R)-yl]-((S)-p-methoxybenzyloxy)-methyl]-5-methyl-tetrahydropyran-4-ol

5-chloro-pentanal

(4R,5R,6R)-5-benzyloxy-4-[1-hydroxy-prop-2-(R)-yl]-2,2,6-trimethyl-1,3-dioxane

Downstream raw materials:

C₆₃H₉₆BClO₁₁Si

C₆₂H₉₄Cl₂O₁₂Si₂

C₆₃H₉₆Cl₂O₁₁Si₂

1-[6-[[4-(tert-butyl-dimethyl-silanyloxy)-6-(4-chloro-butyl)-2-methoxy-5-methyl-tetrahydro-pyran-2-yl]-(4-methoxy-benzyloxy)-methyl]-3,4-bis-(4-methoxy-benzyloxy)-5-methyl-tetrahydro-pyran-2-yl]-7-chloro-4-hydroxy-octa-5,7-dien-2-one

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