methyl 2,3-di-O-(tert-butyldimethylsilyl)-6-deoxy-4-O-((2R)-2-ethoxycarbonyl-2-formylmethylpropanoyl)-α-D-glucopyranoside

Base Information

Chemical Name:methyl 2,3-di-O-(tert-butyldimethylsilyl)-6-deoxy-4-O-((2R)-2-ethoxycarbonyl-2-formylmethylpropanoyl)-α-D-glucopyranoside
CAS No.:1428979-98-9
Molecular Formula:C₂₇H₅₂O₉Si₂
Molecular Weight:576.875
Hs Code.:

Synonyms:methyl 2,3-di-O-(tert-butyldimethylsilyl)-6-deoxy-4-O-((2R)-2-ethoxycarbonyl-2-formylmethylpropanoyl)-α-D-glucopyranoside

Suppliers and Price of methyl 2,3-di-O-(tert-butyldimethylsilyl)-6-deoxy-4-O-((2R)-2-ethoxycarbonyl-2-formylmethylpropanoyl)-α-D-glucopyranoside

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

Chemical Property of methyl 2,3-di-O-(tert-butyldimethylsilyl)-6-deoxy-4-O-((2R)-2-ethoxycarbonyl-2-formylmethylpropanoyl)-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of methyl 2,3-di-O-(tert-butyldimethylsilyl)-6-deoxy-4-O-((2R)-2-ethoxycarbonyl-2-formylmethylpropanoyl)-α-D-glucopyranoside

There total 1 articles about methyl 2,3-di-O-(tert-butyldimethylsilyl)-6-deoxy-4-O-((2R)-2-ethoxycarbonyl-2-formylmethylpropanoyl)-α-D-glucopyranoside 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:

: 2985-33-3
monoethyl methylmalonate

: 1428979-98-9
methyl 2,3-di-O-(tert-butyldimethylsilyl)-6-deoxy-4-O-((2R)-2-ethoxycarbonyl-2-formylmethylpropanoyl)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 15 h / 20 °C

1.2: 3 h / 20 °C

2.1: sodium ethanolate / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere

2.2: 17.5 h / -78 - 0 °C / Inert atmosphere

3.1: ozone / dichloromethane / 0.17 h / -78 °C

3.2: 1.5 h / 0 - 20 °C

With dmap; sodium ethanolate; ozone; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;
DOI:10.1038/ja.2012.124

Reference yield:

: 1428979-98-9
methyl 2,3-di-O-(tert-butyldimethylsilyl)-6-deoxy-4-O-((2R)-2-ethoxycarbonyl-2-formylmethylpropanoyl)-α-D-glucopyranoside

: 1428980-13-5
(2R,5R)-2-((1,3-dioxolan-2-yl)methyl)-2,4,5-trimethylcycohex-3-en-1-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: toluene-4-sulfonic acid / benzene / 3 h / 70 °C

2.1: diisobutylaluminium hydride / toluene / 0.5 h / -78 °C / Inert atmosphere

3.1: 4-methylmorpholine N-oxide / dichloromethane / 0.17 h / 20 °C / Inert atmosphere; Molecular sieve

3.2: 1 h / 20 °C / Inert atmosphere; Molecular sieve

4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

4.2: 1 h / -78 - 0 °C

5.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.75 h / -18 - 20 °C / Inert atmosphere

6.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C

7.1: magnesium; ethylene dibromide / tetrahydrofuran / 1 h / Inert atmosphere; Reflux

7.2: 1 h / 20 °C / Inert atmosphere

8.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C

9.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 18 h / 80 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; n-butyllithium; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; magnesium; 4-methylmorpholine N-oxide; ethylene dibromide; In tetrahydrofuran; dichloromethane; toluene; benzene;
DOI:10.1038/ja.2012.124

Reference yield:

: 1428979-98-9
methyl 2,3-di-O-(tert-butyldimethylsilyl)-6-deoxy-4-O-((2R)-2-ethoxycarbonyl-2-formylmethylpropanoyl)-α-D-glucopyranoside

: 1428980-14-6
(1S,2R,5R)-2-((1,3-dioxolan-2-yl)methyl)-1(2-(ethoxycarbonyl)ethynyl)-2,4,5-trimethylcyclohex-3-en-1-ol

Guidance literature:: Multi-step reaction with 10 steps

1.1: toluene-4-sulfonic acid / benzene / 3 h / 70 °C

2.1: diisobutylaluminium hydride / toluene / 0.5 h / -78 °C / Inert atmosphere

3.1: 4-methylmorpholine N-oxide / dichloromethane / 0.17 h / 20 °C / Inert atmosphere; Molecular sieve

3.2: 1 h / 20 °C / Inert atmosphere; Molecular sieve

4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

4.2: 1 h / -78 - 0 °C

5.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.75 h / -18 - 20 °C / Inert atmosphere

6.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C

7.1: magnesium; ethylene dibromide / tetrahydrofuran / 1 h / Inert atmosphere; Reflux

7.2: 1 h / 20 °C / Inert atmosphere

8.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C

9.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 18 h / 80 °C / Inert atmosphere

10.1: tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

10.2: 1 h / -78 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; n-butyllithium; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; magnesium; 4-methylmorpholine N-oxide; ethylene dibromide; In tetrahydrofuran; hexane; dichloromethane; toluene; benzene;
DOI:10.1038/ja.2012.124