(2R,3R,5R,7S,8R,9R)-9-(benzoyloxy)-7-[2-(tert-butyldiphenylsiloxy)ethyl]-2-[(1S,3S,4R)-3-(benzoyloxy)-1-methoxy-4-methylhex-5-enyl]-3-(2-methoxyethoxymethyl)oxy-4,4,8-trimethyl-1,6-dioxaspiro[4,5]decane

Base Information

Chemical Name:(2R,3R,5R,7S,8R,9R)-9-(benzoyloxy)-7-[2-(tert-butyldiphenylsiloxy)ethyl]-2-[(1S,3S,4R)-3-(benzoyloxy)-1-methoxy-4-methylhex-5-enyl]-3-(2-methoxyethoxymethyl)oxy-4,4,8-trimethyl-1,6-dioxaspiro[4,5]decane
CAS No.:180590-87-8
Molecular Formula:C₅₅H₇₂O₁₁Si
Molecular Weight:937.256
Hs Code.:

(2R,3R,5R,7S,8R,9R)-9-(benzoyloxy)-7-[2-(tert-butyldiphenylsiloxy)ethyl]-2-[(1S,3S,4R)-3-(benzoyloxy)-1-methoxy-4-methylhex-5-enyl]-3-(2-methoxyethoxymethyl)oxy-4,4,8-trimethyl-1,6-dioxaspiro[4,5]decane

Synonyms:(2R,3R,5R,7S,8R,9R)-9-(benzoyloxy)-7-[2-(tert-butyldiphenylsiloxy)ethyl]-2-[(1S,3S,4R)-3-(benzoyloxy)-1-methoxy-4-methylhex-5-enyl]-3-(2-methoxyethoxymethyl)oxy-4,4,8-trimethyl-1,6-dioxaspiro[4,5]decane

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Chemical Property of (2R,3R,5R,7S,8R,9R)-9-(benzoyloxy)-7-[2-(tert-butyldiphenylsiloxy)ethyl]-2-[(1S,3S,4R)-3-(benzoyloxy)-1-methoxy-4-methylhex-5-enyl]-3-(2-methoxyethoxymethyl)oxy-4,4,8-trimethyl-1,6-dioxaspiro[4,5]decane

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Technology Process of (2R,3R,5R,7S,8R,9R)-9-(benzoyloxy)-7-[2-(tert-butyldiphenylsiloxy)ethyl]-2-[(1S,3S,4R)-3-(benzoyloxy)-1-methoxy-4-methylhex-5-enyl]-3-(2-methoxyethoxymethyl)oxy-4,4,8-trimethyl-1,6-dioxaspiro[4,5]decane

There total 8 articles about (2R,3R,5R,7S,8R,9R)-9-(benzoyloxy)-7-[2-(tert-butyldiphenylsiloxy)ethyl]-2-[(1S,3S,4R)-3-(benzoyloxy)-1-methoxy-4-methylhex-5-enyl]-3-(2-methoxyethoxymethyl)oxy-4,4,8-trimethyl-1,6-dioxaspiro[4,5]decane 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: 99.0%

: 98-88-4
benzoyl chloride

: 180590-86-7
Benzoic acid (2R,3R,5R,7S,8R,9R)-7-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-((1S,3S,4R)-3-hydroxy-1-methoxy-4-methyl-hex-5-enyl)-3-(2-methoxy-ethoxymethoxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-9-yl ester

: 180590-87-8
(2R,3R,5R,7S,8R,9R)-9-(benzoyloxy)-7-[2-(tert-butyldiphenylsiloxy)ethyl]-2-[(1S,3S,4R)-3-(benzoyloxy)-1-methoxy-4-methylhex-5-enyl]-3-(2-methoxyethoxymethyl)oxy-4,4,8-trimethyl-1,6-dioxaspiro[4,5]decane

Guidance literature:: With pyridine; at 60 ℃; for 2h;
DOI:10.1021/jo960314y

Reference yield:

: 180590-83-4
Benzoic acid (2S,3R,5R,7S,8R,9R)-2-but-3-enoyl-7-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-(2-methoxy-ethoxymethoxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-9-yl ester

: 180590-87-8
(2R,3R,5R,7S,8R,9R)-9-(benzoyloxy)-7-[2-(tert-butyldiphenylsiloxy)ethyl]-2-[(1S,3S,4R)-3-(benzoyloxy)-1-methoxy-4-methylhex-5-enyl]-3-(2-methoxyethoxymethyl)oxy-4,4,8-trimethyl-1,6-dioxaspiro[4,5]decane

Guidance literature:: Multi-step reaction with 5 steps

1: 85 percent / LiBH₄ / tetrahydrofuran / 1 h / -10 °C

2: 1.) 18-crown-6, potassium hydride / 1) THF, 0 deg C, 5 min; 2) THF, 25 deg C, 12 h

3: 1.) O₃, 2.) Me₂S / 1) CH₃OH, CH₂Cl₂, -78 deg C; 2) CH₂Cl₂, CH₃OH, 25 deg C, 12 h

4: 1.) potassium tert-butoxide, n-BuLi, 2.) (+)-B-methoxydiisopinocampheylborane, 3.) BF₃*Et₂O

5: 99 percent / pyridine / 2 h / 60 °C

With pyridine; (+)-Ipc₂BOMe; lithium borohydride; n-butyllithium; 18-crown-6 ether; dimethylsulfide; boron trifluoride diethyl etherate; potassium tert-butylate; potassium hydride; ozone; In tetrahydrofuran;
DOI:10.1021/jo960314y

Reference yield:

: 180590-81-2
Benzoic acid (2S,3R,5R,7S,8R,9R)-7-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-formyl-3-(2-methoxy-ethoxymethoxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-9-yl ester

: 180590-87-8
(2R,3R,5R,7S,8R,9R)-9-(benzoyloxy)-7-[2-(tert-butyldiphenylsiloxy)ethyl]-2-[(1S,3S,4R)-3-(benzoyloxy)-1-methoxy-4-methylhex-5-enyl]-3-(2-methoxyethoxymethyl)oxy-4,4,8-trimethyl-1,6-dioxaspiro[4,5]decane

Guidance literature:: Multi-step reaction with 7 steps

1: 88.8 percent / ZnCl₂ / tetrahydrofuran; CH₂Cl₂ / 0.25 h / -78 °C

2: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1) CH₂Cl₂, -40 deg C, 10 min; 2) CH₂Cl₂, -78 deg C --> rt

3: 85 percent / LiBH₄ / tetrahydrofuran / 1 h / -10 °C

4: 1.) 18-crown-6, potassium hydride / 1) THF, 0 deg C, 5 min; 2) THF, 25 deg C, 12 h

5: 1.) O₃, 2.) Me₂S / 1) CH₃OH, CH₂Cl₂, -78 deg C; 2) CH₂Cl₂, CH₃OH, 25 deg C, 12 h

6: 1.) potassium tert-butoxide, n-BuLi, 2.) (+)-B-methoxydiisopinocampheylborane, 3.) BF₃*Et₂O

7: 99 percent / pyridine / 2 h / 60 °C

With pyridine; (+)-Ipc₂BOMe; lithium borohydride; n-butyllithium; oxalyl dichloride; 18-crown-6 ether; dimethylsulfide; boron trifluoride diethyl etherate; potassium tert-butylate; potassium hydride; ozone; dimethyl sulfoxide; triethylamine; zinc(II) chloride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo960314y