[(2S,4S,5R,6S)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-acetic acid methyl ester

Base Information

• Chemical Name: [(2S,4S,5R,6S)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-acetic acid methyl ester
• CAS No.: 406684-08-0
• Molecular Formula: C₂₉H₄₂O₆Si
• Molecular Weight: 514.734
• Mol file: 406684-08-0.mol

Synonyms:[(2S,4S,5R,6S)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-acetic acid methyl ester

Chemical Property of [(2S,4S,5R,6S)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-acetic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2S,4S,5R,6S)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-acetic acid methyl ester

There total 3 articles about [(2S,4S,5R,6S)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-acetic 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:

tert-butyldimethylsilyl chloride (18162-48-6) → [(2S,4S,5R,6S)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-acetic acid methyl ester (406684-08-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: HCl / methanol / 8 h / 0 - 20 °C

1.2: imidazole / CH₂Cl₂ / 0.17 h / 20 °C

1.3: 87 percent / N-methylmorpholine / CH₂Cl₂ / 2 h / 20 °C

2.1: (C₆H₅)I(OCOCF₃)2; NaHCO₃ / acetonitrile; H₂O / 0.08 h / 0 °C

2.2: NaBH₄ / acetonitrile; H₂O / 0.5 h / 0 °C

2.3: 79 percent / CBr₄; P(C₆H₅)3; N(C₂H₅)3 / CH₂Cl₂ / 2 h / 0 - 20 °C

3.1: (C₄H₉)3Sn / AIBN / benzene / 2 h / Heating

With hydrogenchloride; (C₄H₉)3Sn; sodium hydrogencarbonate; bis-[(trifluoroacetoxy)iodo]benzene; 2,2'-azobis(isobutyronitrile); In methanol; water; acetonitrile; benzene;

DOI:10.1002/1521-3773(20020104)41:1<176::AID-ANIE176>3.0.CO;2-#

Reference yield:

(E)-3-[(1S,2S,3R)-2,3-Bis-benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-4,4-bis-ethylsulfanyl-butoxy]-acrylic acid methyl ester (406684-06-8) → [(2S,4S,5R,6S)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-acetic acid methyl ester (406684-08-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: (C₆H₅)I(OCOCF₃)2; NaHCO₃ / acetonitrile; H₂O / 0.08 h / 0 °C

1.2: NaBH₄ / acetonitrile; H₂O / 0.5 h / 0 °C

1.3: 79 percent / CBr₄; P(C₆H₅)3; N(C₂H₅)3 / CH₂Cl₂ / 2 h / 0 - 20 °C

2.1: (C₄H₉)3Sn / AIBN / benzene / 2 h / Heating

With (C₄H₉)3Sn; sodium hydrogencarbonate; bis-[(trifluoroacetoxy)iodo]benzene; 2,2'-azobis(isobutyronitrile); In water; acetonitrile; benzene;

DOI:10.1002/1521-3773(20020104)41:1<176::AID-ANIE176>3.0.CO;2-#

Reference yield:

(E)-3-[(1S,2S,3R)-2,3-Bis-benzyloxy-4-bromo-1-(tert-butyl-dimethyl-silanyloxymethyl)-butoxy]-acrylic acid methyl ester (406684-07-9) → [(2S,4S,5R,6S)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-acetic acid methyl ester (406684-08-0) + [(2R,4S,5R,6S)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-acetic acid methyl ester

Guidance literature:

With (C₄H₉)3Sn; 2,2'-azobis(isobutyronitrile); In benzene; for 2h; Heating;

DOI:10.1002/1521-3773(20020104)41:1<176::AID-ANIE176>3.0.CO;2-#

upstream raw materials:

(E)-3-[(1S,2S,3R)-2,3-Bis-benzyloxy-4-bromo-1-(tert-butyl-dimethyl-silanyloxymethyl)-butoxy]-acrylic acid methyl ester

tert-butyldimethylsilyl chloride

(E)-3-[(1S,2S,3R)-2,3-Bis-benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-4,4-bis-ethylsulfanyl-butoxy]-acrylic acid methyl ester

Downstream raw materials:

[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]aldehyde

(+)-ambruticin S

methyl (8E,10S,11S,12S)-2,3-di-O-benzyl-1,4-dideoxy-1β-<11-methyl-12-formylcyclopropylethenyl>-D-glucoheptopyranuronate

methyl 5β,6α-dibenzyloxypolyangioate