(5R,6S,7S,8R)-8-(tert-Butyl-dimethyl-silanyloxy)-7-((E)-2-methoxy-vinyl)-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester

Base Information

Chemical Name:(5R,6S,7S,8R)-8-(tert-Butyl-dimethyl-silanyloxy)-7-((E)-2-methoxy-vinyl)-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester
CAS No.:303958-10-3
Molecular Formula:C₃₁H₄₂O₉Si
Molecular Weight:586.755
Hs Code.:

(5R,6S,7S,8R)-8-(tert-Butyl-dimethyl-silanyloxy)-7-((E)-2-methoxy-vinyl)-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester

Synonyms:(5R,6S,7S,8R)-8-(tert-Butyl-dimethyl-silanyloxy)-7-((E)-2-methoxy-vinyl)-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester

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Chemical Property of (5R,6S,7S,8R)-8-(tert-Butyl-dimethyl-silanyloxy)-7-((E)-2-methoxy-vinyl)-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester

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Technology Process of (5R,6S,7S,8R)-8-(tert-Butyl-dimethyl-silanyloxy)-7-((E)-2-methoxy-vinyl)-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester

There total 7 articles about (5R,6S,7S,8R)-8-(tert-Butyl-dimethyl-silanyloxy)-7-((E)-2-methoxy-vinyl)-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester 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: 68.0%

: 4009-98-7
(methoxymethyl)triphenylphosphonium chloride

: 303958-08-9
8-(tert-butyl-dimethyl-silanyloxy)-7-formyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester

: 303958-10-3
(5R,6S,7S,8R)-8-(tert-Butyl-dimethyl-silanyloxy)-7-((E)-2-methoxy-vinyl)-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester

Guidance literature:: With n-butyllithium; In tetrahydrofuran; at -40 - 25 ℃;
DOI:10.1016/S0040-4039(00)01136-9

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 303958-10-3
(5R,6S,7S,8R)-8-(tert-Butyl-dimethyl-silanyloxy)-7-((E)-2-methoxy-vinyl)-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

2: 100 percent / aq. NaOH / tetrahydrofuran / 0 °C

3: Dess-Martin periodinane / CH₂Cl₂ / 25 °C

4: K₂CO₃ / acetone / 25 °C

5: 68 percent / n-BuLi / tetrahydrofuran / -40 - 25 °C

With 2,6-dimethylpyridine; sodium hydroxide; n-butyllithium; potassium carbonate; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; acetone; 1: silylation / 2: Hydrolysis / 3: Oxidation / 4: oxidative esterification / 5: Wittig methylenation;
DOI:10.1016/S0040-4039(00)01136-9

Reference yield:

: 112711-16-7
(5R,5aR,8aR,9R)-9-((tert-butyldimethylsilyl)oxy)-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one

: 303958-10-3
(5R,6S,7S,8R)-8-(tert-Butyl-dimethyl-silanyloxy)-7-((E)-2-methoxy-vinyl)-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 100 percent / aq. NaOH / tetrahydrofuran / 0 °C

2: Dess-Martin periodinane / CH₂Cl₂ / 25 °C

3: K₂CO₃ / acetone / 25 °C

4: 68 percent / n-BuLi / tetrahydrofuran / -40 - 25 °C

With sodium hydroxide; n-butyllithium; potassium carbonate; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; acetone; 1: Hydrolysis / 2: Oxidation / 3: oxidative esterification / 4: Wittig methylenation;
DOI:10.1016/S0040-4039(00)01136-9