Benzoic acid (2S,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-furan-2-yl-6-methoxy-2-((Z)-2-methoxycarbonyl-vinyl)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2S,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-furan-2-yl-6-methoxy-2-((Z)-2-methoxycarbonyl-vinyl)-tetrahydro-pyran-3-yl ester
• CAS No.: 102682-12-2
• Molecular Formula: C₂₇H₃₆O₈Si
• Molecular Weight: 516.664
• Mol file: 102682-12-2.mol

Synonyms:

Chemical Property of Benzoic acid (2S,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-furan-2-yl-6-methoxy-2-((Z)-2-methoxycarbonyl-vinyl)-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2S,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-furan-2-yl-6-methoxy-2-((Z)-2-methoxycarbonyl-vinyl)-tetrahydro-pyran-3-yl ester

There total 16 articles about Benzoic acid (2S,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-furan-2-yl-6-methoxy-2-((Z)-2-methoxycarbonyl-vinyl)-tetrahydro-pyran-3-yl 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: 71.0%

bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate (88738-78-7) + Benzoic acid (2R,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-2-formyl-6-furan-2-yl-6-methoxy-tetrahydro-pyran-3-yl ester (114027-47-3) → Benzoic acid (2S,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-furan-2-yl-6-methoxy-2-((Z)-2-methoxycarbonyl-vinyl)-tetrahydro-pyran-3-yl ester (102682-12-2,113974-06-4)

Guidance literature:

With 18-crown-6 ether; potassium hexamethylsilazane; acetonitrile; In tetrahydrofuran; toluene; at -78 ℃; for 0.5h;

DOI:10.1021/ja00220a035

Reference yield:

Benzoic acid (Z)-4-furan-2-yl-4-hydroxy-2-oxo-but-3-enyl ester (113892-49-2) → Benzoic acid (2S,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-furan-2-yl-6-methoxy-2-((Z)-2-methoxycarbonyl-vinyl)-tetrahydro-pyran-3-yl ester (102682-12-2,113974-06-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 3.6 g / diethyl ether / 1 h / 0 °C

2: triethylamine / diethyl ether / 1.) 0 gradC, 5 min; 2.) roomtemp., 30 min

3: 1.) Dibal; 2.) DMF; 3.) BF₃*OEt₂; 4.) trifluoroacetic acid

4: ceric chloride heptahydrate, NaBH₄ / CH₂Cl₂; ethanol / 1 h / -78 °C

5: 90 percent / CSA / methanol; benzene / 3 h / 25 °C

6: 93 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

7: 96 percent / H₂O₂, pyridine / tetrahydrofuran / 4 h / Ambient temperature

8: 1.) osmium tetraoxide, NMO; 2.) Florisil, NaHSO₃ / 1.) THF-water, 2 h; 2.) THF-water, roomtemp., 1 h

9: NaHCO₃, Pb(OAc)4 / CH₂Cl₂ / 0.17 h / 0 °C

10: 71 percent / KHMDS, 18-crown-6/acetonitrile complex / tetrahydrofuran; toluene / 0.5 h / -78 °C

With pyridine; 2,6-dimethylpyridine; lead(IV) acetate; sodium tetrahydroborate; florisil; osmium(VIII) oxide; N-methyl-2-indolinone; 18-crown-6 ether; ceric chloride heptahydrate; boron trifluoride diethyl etherate; dihydrogen peroxide; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; sodium hydrogensulfite; triethylamine; N,N-dimethyl-formamide; acetonitrile; trifluoroacetic acid; camphor-10-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; toluene; benzene;

DOI:10.1021/ja00220a035

Reference yield:

Benzoic acid (Z)-4-furan-2-yl-4-methoxy-2-oxo-but-3-enyl ester (92622-30-5) → Benzoic acid (2S,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-furan-2-yl-6-methoxy-2-((Z)-2-methoxycarbonyl-vinyl)-tetrahydro-pyran-3-yl ester (102682-12-2,113974-06-4)

Guidance literature:

Multi-step reaction with 9 steps

1: triethylamine / diethyl ether / 1.) 0 gradC, 5 min; 2.) roomtemp., 30 min

2: 1.) Dibal; 2.) DMF; 3.) BF₃*OEt₂; 4.) trifluoroacetic acid

3: ceric chloride heptahydrate, NaBH₄ / CH₂Cl₂; ethanol / 1 h / -78 °C

4: 90 percent / CSA / methanol; benzene / 3 h / 25 °C

5: 93 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

6: 96 percent / H₂O₂, pyridine / tetrahydrofuran / 4 h / Ambient temperature

7: 1.) osmium tetraoxide, NMO; 2.) Florisil, NaHSO₃ / 1.) THF-water, 2 h; 2.) THF-water, roomtemp., 1 h

8: NaHCO₃, Pb(OAc)4 / CH₂Cl₂ / 0.17 h / 0 °C

9: 71 percent / KHMDS, 18-crown-6/acetonitrile complex / tetrahydrofuran; toluene / 0.5 h / -78 °C

With pyridine; 2,6-dimethylpyridine; lead(IV) acetate; sodium tetrahydroborate; florisil; osmium(VIII) oxide; N-methyl-2-indolinone; 18-crown-6 ether; ceric chloride heptahydrate; boron trifluoride diethyl etherate; dihydrogen peroxide; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; sodium hydrogensulfite; triethylamine; N,N-dimethyl-formamide; acetonitrile; trifluoroacetic acid; camphor-10-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; toluene; benzene;

DOI:10.1021/ja00220a035

upstream raw materials:

bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate

Benzoic acid (2R,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-2-formyl-6-furan-2-yl-6-methoxy-tetrahydro-pyran-3-yl ester

Benzoic acid (2S,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-furan-2-yl-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yl ester

Benzoic acid (2S,3R,4S,6S)-2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-6-furan-2-yl-6-methoxy-tetrahydro-pyran-3-yl ester

Downstream raw materials:

Benzoic acid (2S,3R,4S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-2-((1R,2S)-1,2-dihydroxy-2-methoxycarbonyl-ethyl)-6-furan-2-yl-6-methoxy-tetrahydro-pyran-3-yl ester

Benzoic acid (2R,3S,4R,6R)-4-(tert-butyl-dimethyl-silanyloxy)-6-furan-2-yl-6-methoxy-2-((1S,2S)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-3-yl ester

(2S,4S,5S,6R)-5-Benzoyloxy-4-hydroxy-2-methoxy-6-((1R,2R)-1,2,3-tris-benzoyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

(2S,4S,5S,6R)-4-Benzoyloxy-5-hydroxy-2-methoxy-6-((1R,2R)-1,2,3-tris-benzoyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester