Chloro-acetic acid (3S,4R,5R,6S)-5-benzyloxy-6-((2S,3S,4R,5R,6R)-4-benzyloxy-3-methoxy-6-methoxymethyl-5-triisopropylsilanyloxy-tetrahydro-pyran-2-yloxy)-4-hydroxy-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Chloro-acetic acid (3S,4R,5R,6S)-5-benzyloxy-6-((2S,3S,4R,5R,6R)-4-benzyloxy-3-methoxy-6-methoxymethyl-5-triisopropylsilanyloxy-tetrahydro-pyran-2-yloxy)-4-hydroxy-tetrahydro-pyran-3-yl ester
• CAS No.: 256342-29-7
• Molecular Formula: C₃₈H₅₇ClO₁₁Si
• Molecular Weight: 753.402

Synonyms:Chloro-acetic acid (3S,4R,5R,6S)-5-benzyloxy-6-((2S,3S,4R,5R,6R)-4-benzyloxy-3-methoxy-6-methoxymethyl-5-triisopropylsilanyloxy-tetrahydro-pyran-2-yloxy)-4-hydroxy-tetrahydro-pyran-3-yl ester

Chemical Property of Chloro-acetic acid (3S,4R,5R,6S)-5-benzyloxy-6-((2S,3S,4R,5R,6R)-4-benzyloxy-3-methoxy-6-methoxymethyl-5-triisopropylsilanyloxy-tetrahydro-pyran-2-yloxy)-4-hydroxy-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Chloro-acetic acid (3S,4R,5R,6S)-5-benzyloxy-6-((2S,3S,4R,5R,6R)-4-benzyloxy-3-methoxy-6-methoxymethyl-5-triisopropylsilanyloxy-tetrahydro-pyran-2-yloxy)-4-hydroxy-tetrahydro-pyran-3-yl ester

There total 22 articles about Chloro-acetic acid (3S,4R,5R,6S)-5-benzyloxy-6-((2S,3S,4R,5R,6R)-4-benzyloxy-3-methoxy-6-methoxymethyl-5-triisopropylsilanyloxy-tetrahydro-pyran-2-yloxy)-4-hydroxy-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:

(1R,2S,3S)-2,3-Bis-allyloxy-4-(tert-butyl-diphenyl-silanyloxy)-1-thiazol-2-yl-butan-1-ol (306726-10-3) → Chloro-acetic acid (3S,4R,5R,6S)-5-benzyloxy-6-((2S,3S,4R,5R,6R)-4-benzyloxy-3-methoxy-6-methoxymethyl-5-triisopropylsilanyloxy-tetrahydro-pyran-2-yloxy)-4-hydroxy-tetrahydro-pyran-3-yl ester (256342-29-7)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 98 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h / 0 - 25 °C

2.1: molecular sieves 4 Angstroem / acetonitrile / 0.25 h / 25 °C

3.1: NaBH₄ / methanol / 0.5 h / 0 °C

3.2: H₂O; CuCl₂; CuO / acetonitrile / 2 h / 25 °C

4.1: 10.97 g / TBAF; AcOH / 2 h / 25 °C

5.1: 85 percent / DBU / CH₂Cl₂ / 0.5 h / 0 °C

6.1: nBu₂SnO / methanol / 3 h / Heating

6.2: TMSOTf / CH₂Cl₂ / 12 h / 0 - 25 °C

6.3: 10.82 g / PPTS; MeOH / 1 h / 25 °C

7.1: 87 percent / NaH / dimethylformamide / 1 h / 0 - 25 °C

8.1: 95 percent / NaOH; MeOH / diethyl ether / 1 h / 25 °C

9.1: NaH / dimethylformamide / 0.08 h / 0 °C

9.2: 90 percent / nBu₄NI / dimethylformamide / 4 h / 0 - 25 °C

10.1: 91 percent / DDQ; H₂O / CH₂Cl₂ / 1 h / 0 - 25 °C

11.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 - 25 °C

12.1: DABCO / [(Ph₃P)3RhCl] / aq. ethanol / 2 h / Heating

13.1: 9.27 g / NMO; OsO₄; H₂O / acetone / 8 h / 25 °C

14.1: nBu₂SnO / toluene / 3 h / Heating

14.2: toluene / 1 h / 0 - 25 °C

With 1,4-diaza-bicyclo[2.2.2]octane; 2,6-dimethylpyridine; methanol; dmap; sodium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; N-methyl-2-indolinone; 4 A molecular sieve; tetrabutyl ammonium fluoride; water; sodium hydride; di(n-butyl)tin oxide; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Wilkinson's catalyst; In methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 1.1: Esterification / 2.1: Methylation / 3.1: Reduction / 3.2: Ring cleavage / 4.1: Cyclization / 5.1: Addition / 6.1: Cyclization / 6.2: Ring cleavage / 6.3: Methanolysis / 7.1: Methylation / 8.1: Debenzoylation / 9.1: Metallation / 9.2: Etherification / 10.1: Oxidation / 11.1: Etherification / 12.1: Isomerization / 13.1: Oxidation / 14.1: Cyclization / 14.2: Ring cleavage;

DOI:10.1002/1521-3765(20000901)6:17<3116::AID-CHEM3116>3.0.CO;2-8

Reference yield:

Benzoic acid (1R,2R,3S)-2,3-bis-allyloxy-4-(tert-butyl-diphenyl-silanyloxy)-1-thiazol-2-yl-butyl ester (306726-12-5) → Chloro-acetic acid (3S,4R,5R,6S)-5-benzyloxy-6-((2S,3S,4R,5R,6R)-4-benzyloxy-3-methoxy-6-methoxymethyl-5-triisopropylsilanyloxy-tetrahydro-pyran-2-yloxy)-4-hydroxy-tetrahydro-pyran-3-yl ester (256342-29-7)

Guidance literature:

Multi-step reaction with 13 steps

1.1: molecular sieves 4 Angstroem / acetonitrile / 0.25 h / 25 °C

2.1: NaBH₄ / methanol / 0.5 h / 0 °C

2.2: H₂O; CuCl₂; CuO / acetonitrile / 2 h / 25 °C

3.1: 10.97 g / TBAF; AcOH / 2 h / 25 °C

4.1: 85 percent / DBU / CH₂Cl₂ / 0.5 h / 0 °C

5.1: nBu₂SnO / methanol / 3 h / Heating

5.2: TMSOTf / CH₂Cl₂ / 12 h / 0 - 25 °C

5.3: 10.82 g / PPTS; MeOH / 1 h / 25 °C

6.1: 87 percent / NaH / dimethylformamide / 1 h / 0 - 25 °C

7.1: 95 percent / NaOH; MeOH / diethyl ether / 1 h / 25 °C

8.1: NaH / dimethylformamide / 0.08 h / 0 °C

8.2: 90 percent / nBu₄NI / dimethylformamide / 4 h / 0 - 25 °C

9.1: 91 percent / DDQ; H₂O / CH₂Cl₂ / 1 h / 0 - 25 °C

10.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 - 25 °C

11.1: DABCO / [(Ph₃P)3RhCl] / aq. ethanol / 2 h / Heating

12.1: 9.27 g / NMO; OsO₄; H₂O / acetone / 8 h / 25 °C

13.1: nBu₂SnO / toluene / 3 h / Heating

13.2: toluene / 1 h / 0 - 25 °C

With 1,4-diaza-bicyclo[2.2.2]octane; 2,6-dimethylpyridine; methanol; sodium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; N-methyl-2-indolinone; 4 A molecular sieve; tetrabutyl ammonium fluoride; water; sodium hydride; di(n-butyl)tin oxide; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Wilkinson's catalyst; In methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 1.1: Methylation / 2.1: Reduction / 2.2: Ring cleavage / 3.1: Cyclization / 4.1: Addition / 5.1: Cyclization / 5.2: Ring cleavage / 5.3: Methanolysis / 6.1: Methylation / 7.1: Debenzoylation / 8.1: Metallation / 8.2: Etherification / 9.1: Oxidation / 10.1: Etherification / 11.1: Isomerization / 12.1: Oxidation / 13.1: Cyclization / 13.2: Ring cleavage;

DOI:10.1002/1521-3765(20000901)6:17<3116::AID-CHEM3116>3.0.CO;2-8

Reference yield:

Benzoic acid (3R,4R,5S)-4,5-bis-allyloxy-2-hydroxy-tetrahydro-pyran-3-yl ester → Chloro-acetic acid (3S,4R,5R,6S)-5-benzyloxy-6-((2S,3S,4R,5R,6R)-4-benzyloxy-3-methoxy-6-methoxymethyl-5-triisopropylsilanyloxy-tetrahydro-pyran-2-yloxy)-4-hydroxy-tetrahydro-pyran-3-yl ester (256342-29-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 85 percent / DBU / CH₂Cl₂ / 0.5 h / 0 °C

2.1: nBu₂SnO / methanol / 3 h / Heating

2.2: TMSOTf / CH₂Cl₂ / 12 h / 0 - 25 °C

2.3: 10.82 g / PPTS; MeOH / 1 h / 25 °C

3.1: 87 percent / NaH / dimethylformamide / 1 h / 0 - 25 °C

4.1: 95 percent / NaOH; MeOH / diethyl ether / 1 h / 25 °C

5.1: NaH / dimethylformamide / 0.08 h / 0 °C

5.2: 90 percent / nBu₄NI / dimethylformamide / 4 h / 0 - 25 °C

6.1: 91 percent / DDQ; H₂O / CH₂Cl₂ / 1 h / 0 - 25 °C

7.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 - 25 °C

8.1: DABCO / [(Ph₃P)3RhCl] / aq. ethanol / 2 h / Heating

9.1: 9.27 g / NMO; OsO₄; H₂O / acetone / 8 h / 25 °C

10.1: nBu₂SnO / toluene / 3 h / Heating

10.2: toluene / 1 h / 0 - 25 °C

With 1,4-diaza-bicyclo[2.2.2]octane; 2,6-dimethylpyridine; methanol; sodium hydroxide; osmium(VIII) oxide; N-methyl-2-indolinone; water; sodium hydride; di(n-butyl)tin oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Wilkinson's catalyst; In methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 1.1: Addition / 2.1: Cyclization / 2.2: Ring cleavage / 2.3: Methanolysis / 3.1: Methylation / 4.1: Debenzoylation / 5.1: Metallation / 5.2: Etherification / 6.1: Oxidation / 7.1: Etherification / 8.1: Isomerization / 9.1: Oxidation / 10.1: Cyclization / 10.2: Ring cleavage;

DOI:10.1002/1521-3765(20000901)6:17<3116::AID-CHEM3116>3.0.CO;2-8

upstream raw materials:

chloroacetyl chloride

(3S,4R,5R,6S)-5-Benzyloxy-6-((2S,3S,4R,5R,6R)-4-benzyloxy-3-methoxy-6-methoxymethyl-5-triisopropylsilanyloxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3,4-diol

benzyl bromide

phenyl 2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside

Downstream raw materials:

C₄₀H₄₈O₁₃

Benzoic acid (2S,3R,4R,5S)-3-benzyloxy-2-((2S,3S,4R,5R,6R)-4-benzyloxy-3-methoxy-6-methoxymethyl-5-triisopropylsilanyloxy-tetrahydro-pyran-2-yloxy)-5-hydroxy-tetrahydro-pyran-4-yl ester

C₃₉H₅₆O₁₄Si

C₄₆H₆₂O₁₃Si

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