(1S,3S,4S,5R,6R)-1-[(2R,3R,5R,7S,8S,9R)-7-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-9-hydroxy-3-(2-methoxy-ethoxymethoxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-2-yl]-1-methoxy-4,6-dimethyl-oct-7-ene-3,5-diol

Base Information

Chemical Name:(1S,3S,4S,5R,6R)-1-[(2R,3R,5R,7S,8S,9R)-7-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-9-hydroxy-3-(2-methoxy-ethoxymethoxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-2-yl]-1-methoxy-4,6-dimethyl-oct-7-ene-3,5-diol
CAS No.:1054641-72-3
Molecular Formula:C₄₄H₇₀O₁₀Si
Molecular Weight:787.119
Hs Code.:

(1S,3S,4S,5R,6R)-1-[(2R,3R,5R,7S,8S,9R)-7-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-9-hydroxy-3-(2-methoxy-ethoxymethoxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-2-yl]-1-methoxy-4,6-dimethyl-oct-7-ene-3,5-diol

Synonyms:(1S,3S,4S,5R,6R)-1-[(2R,3R,5R,7S,8S,9R)-7-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-9-hydroxy-3-(2-methoxy-ethoxymethoxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-2-yl]-1-methoxy-4,6-dimethyl-oct-7-ene-3,5-diol

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Chemical Property of (1S,3S,4S,5R,6R)-1-[(2R,3R,5R,7S,8S,9R)-7-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-9-hydroxy-3-(2-methoxy-ethoxymethoxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-2-yl]-1-methoxy-4,6-dimethyl-oct-7-ene-3,5-diol

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Technology Process of (1S,3S,4S,5R,6R)-1-[(2R,3R,5R,7S,8S,9R)-7-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-9-hydroxy-3-(2-methoxy-ethoxymethoxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-2-yl]-1-methoxy-4,6-dimethyl-oct-7-ene-3,5-diol

There total 11 articles about (1S,3S,4S,5R,6R)-1-[(2R,3R,5R,7S,8S,9R)-7-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-9-hydroxy-3-(2-methoxy-ethoxymethoxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-2-yl]-1-methoxy-4,6-dimethyl-oct-7-ene-3,5-diol 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:

: 180590-88-9
(3R,4R,5S,6S,8S,8(2R,3R,5R,7S,8R,9R))-8-(9-[(benzoyl)oxy]-7-[2-(tert-butyldiphenylsiloxy)ethyl]-3-{[(2-methoxyethoxy)methyl]oxy}4,4,8-trimethyl-1,6-dioxaspiro[4,5]dec-2-yl)-6-(benzoyloxy)-4-hydroxy-8-methoxy-3,5-dimethyloct-1-ene

: 1054641-72-3
(1S,3S,4S,5R,6R)-1-[(2R,3R,5R,7S,8S,9R)-7-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-9-hydroxy-3-(2-methoxy-ethoxymethoxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-2-yl]-1-methoxy-4,6-dimethyl-oct-7-ene-3,5-diol

Guidance literature:: With allylmagnesium bromide; In diethyl ether; dichloromethane; at -78 - 25 ℃; for 0.5h;
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

: 1054641-72-3
(1S,3S,4S,5R,6R)-1-[(2R,3R,5R,7S,8S,9R)-7-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-9-hydroxy-3-(2-methoxy-ethoxymethoxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-2-yl]-1-methoxy-4,6-dimethyl-oct-7-ene-3,5-diol

Guidance literature:: Multi-step reaction with 10 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

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

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

10: allylmagnesium bromide / CH₂Cl₂; diethyl ether / 0.5 h / -78 - 25 °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; allylmagnesium bromide; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/jo960314y

Reference yield:

: 180590-80-1
Benzoic acid (2R,3R,5R,7S,8R,9R)-7-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-hydroxymethyl-3-(2-methoxy-ethoxymethoxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-9-yl ester

: 1054641-72-3
(1S,3S,4S,5R,6R)-1-[(2R,3R,5R,7S,8S,9R)-7-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-9-hydroxy-3-(2-methoxy-ethoxymethoxy)-4,4,8-trimethyl-1,6-dioxa-spiro[4.5]dec-2-yl]-1-methoxy-4,6-dimethyl-oct-7-ene-3,5-diol

Guidance literature:: Multi-step reaction with 11 steps

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

2: 88.8 percent / ZnCl₂ / tetrahydrofuran; CH₂Cl₂ / 0.25 h / -78 °C

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

4: 85 percent / LiBH₄ / tetrahydrofuran / 1 h / -10 °C

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

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

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

8: 99 percent / pyridine / 2 h / 60 °C

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

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

11: allylmagnesium bromide / CH₂Cl₂; diethyl ether / 0.5 h / -78 - 25 °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; allylmagnesium bromide; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/jo960314y