Acetic acid (1S,4S,5R,6R)-5-benzyloxy-4-[(2R,4aR,6R,7R,8S,8aR)-7,8-bis-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-6-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enyl ester

Base Information

• Chemical Name: Acetic acid (1S,4S,5R,6R)-5-benzyloxy-4-[(2R,4aR,6R,7R,8S,8aR)-7,8-bis-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-6-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enyl ester
• CAS No.: 144225-87-6
• Molecular Formula: C₄₆H₇₄O₁₀Si₃
• Molecular Weight: 871.344

Synonyms:

Chemical Property of Acetic acid (1S,4S,5R,6R)-5-benzyloxy-4-[(2R,4aR,6R,7R,8S,8aR)-7,8-bis-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-6-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of Acetic acid (1S,4S,5R,6R)-5-benzyloxy-4-[(2R,4aR,6R,7R,8S,8aR)-7,8-bis-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-6-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enyl ester

There total 9 articles about Acetic acid (1S,4S,5R,6R)-5-benzyloxy-4-[(2R,4aR,6R,7R,8S,8aR)-7,8-bis-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-6-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enyl 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:

t-butyldimethylsiyl triflate (69739-34-0) → Acetic acid (1R,4R,5S,6S)-5-benzyloxy-4-[(2R,4aR,6R,7R,8S,8aR)-7,8-bis-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-6-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enyl ester (144225-87-6,144300-79-8)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / benzene / 5 h / Ambient temperature

2: NaBH₄, CeCl₃*7H₂O / methanol / 2 h / 0 °C

3: Et₃N, DMAP / CH₂Cl₂

With dmap; sodium tetrahydroborate; cerium(III) chloride; triethylamine; In methanol; dichloromethane; benzene;

DOI:10.1021/jo00049a007

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → Acetic acid (1S,4S,5R,6R)-5-benzyloxy-4-[(2R,4aR,6R,7R,8S,8aR)-7,8-bis-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-6-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enyl ester (144225-87-6,144300-79-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / Et₃N / toluene / a) -23 deg C, b) r.t., 7 h

2: LiAl(OtBu)3H / tetrahydrofuran / 24 h / -78 deg C to r.t.

3: Et₃N, DMAP / CH₂Cl₂

With dmap; lithium tri-t-butoxyaluminum hydride; triethylamine; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/jo00049a007

Reference yield:

(1R,4R,5R,6S)-6-Benzyloxy-5-[(2R,4aR,6S,7R,8S,8aR)-7,8-bis-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-7-oxa-bicyclo[2.2.1]heptan-2-one → Acetic acid (1R,4R,5S,6S)-5-benzyloxy-4-[(2R,4aR,6R,7R,8S,8aR)-7,8-bis-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-6-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enyl ester (144225-87-6,144300-79-8)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / benzene / 5 h / Ambient temperature

2: NaBH₄, CeCl₃*7H₂O / methanol / 2 h / 0 °C

3: Et₃N, DMAP / CH₂Cl₂

With dmap; sodium tetrahydroborate; cerium(III) chloride; triethylamine; In methanol; dichloromethane; benzene;

DOI:10.1021/jo00049a007

upstream raw materials:

acetic anhydride

t-butyldimethylsiyl triflate

(4R,5S,6R)-5-Benzyloxy-4-[(2R,4aR,6R,7R,8S,8aR)-7,8-bis-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-6-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enone

(1R,4R,5R,6S)-6-Benzyloxy-5-((2R,4aR,6S,7R,8R,8aS)-7,8-dihydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-7-oxa-bicyclo[2.2.1]heptan-2-one

Downstream raw materials:

Acetic acid (1R,2R,3S,4R,5R,6S)-3-benzyloxy-4-[(2R,4aR,6S,7R,8S,8aR)-7,8-bis-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-2-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydroxy-cyclohexyl ester

Acetic acid (1R,2R,3S,4R,5S,6R)-3-benzyloxy-4-[(2R,4aR,6S,7R,8S,8aR)-7,8-bis-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-2-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydroxy-cyclohexyl ester

Acetic acid (1S,2S,3R,4S,5R,6S)-3-benzyloxy-4-[(2R,4aR,6S,7R,8S,8aR)-7,8-bis-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-2-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydroxy-cyclohexyl ester

Acetic acid (1S,2S,3R,4S,5S,6R)-3-benzyloxy-4-[(2R,4aR,6S,7R,8S,8aR)-7,8-bis-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-2-(tert-butyl-dimethyl-silanyloxy)-5,6-dihydroxy-cyclohexyl ester

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