[(2S,3S,4R,4aR,5aR,9R,10aS,11aR)-3,4-Bis-benzyloxy-2-(2-oxo-propyl)-7-triethylsilanyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-yl]-acetic acid

Base Information

• Chemical Name: [(2S,3S,4R,4aR,5aR,9R,10aS,11aR)-3,4-Bis-benzyloxy-2-(2-oxo-propyl)-7-triethylsilanyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-yl]-acetic acid
• CAS No.: 344315-32-8
• Molecular Formula: C₃₇H₅₀O₈Si
• Molecular Weight: 650.885

Synonyms:[(2S,3S,4R,4aR,5aR,9R,10aS,11aR)-3,4-Bis-benzyloxy-2-(2-oxo-propyl)-7-triethylsilanyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-yl]-acetic acid

Chemical Property of [(2S,3S,4R,4aR,5aR,9R,10aS,11aR)-3,4-Bis-benzyloxy-2-(2-oxo-propyl)-7-triethylsilanyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-yl]-acetic acid

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Technology Process of [(2S,3S,4R,4aR,5aR,9R,10aS,11aR)-3,4-Bis-benzyloxy-2-(2-oxo-propyl)-7-triethylsilanyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-yl]-acetic acid

There total 32 articles about [(2S,3S,4R,4aR,5aR,9R,10aS,11aR)-3,4-Bis-benzyloxy-2-(2-oxo-propyl)-7-triethylsilanyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-yl]-acetic acid 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: 88.0%

2-((2S,3S,4R,4aR,5aR,9R,10aS,11aR)-2-Allyl-3,4-bis-benzyloxy-7-triethylsilanyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-yl)-ethanol (344315-31-7) → [(2S,3S,4R,4aR,5aR,9R,10aS,11aR)-3,4-Bis-benzyloxy-2-(2-oxo-propyl)-7-triethylsilanyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-yl]-acetic acid (344315-32-8)

Guidance literature:

2-((2S,3S,4R,4aR,5aR,9R,10aS,11aR)-2-Allyl-3,4-bis-benzyloxy-7-triethylsilanyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-yl)-ethanol; With jones' reagent; In acetone;

With copper(l) chloride; palladium dichloride; In water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)00286-6

Reference yield:

1-[(2S,3S,4R,4aR,5aR,9R,10aS,11aR)-3,4-Bis-benzyloxy-9-(2-hydroxy-ethyl)-7-triethylsilanyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl]-propan-2-one (440339-80-0) → [(2S,3S,4R,4aR,5aR,9R,10aS,11aR)-3,4-Bis-benzyloxy-2-(2-oxo-propyl)-7-triethylsilanyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-yl]-acetic acid (344315-32-8)

Guidance literature:

With jones' reagent; In acetone; at 0 ℃; for 0.5h;

DOI:10.1016/S0040-4020(02)00044-3

Reference yield:

(2R,3S,4aR,6S,7S,8R,8aR)-6-Allyl-7,8-bis-benzyloxy-2-[4-hydroxy-6-(4-methoxy-benzyloxy)-hex-2-ynyl]-octahydro-pyrano[3,2-b]pyran-3-ol (344315-30-6) → [(2S,3S,4R,4aR,5aR,9R,10aS,11aR)-3,4-Bis-benzyloxy-2-(2-oxo-propyl)-7-triethylsilanyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-yl]-acetic acid (344315-32-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Co₂(CO)8 / CH₂Cl₂ / 0.33 h / 20 °C

1.2: BF₃*OEt₂ / CH₂Cl₂ / 0.25 h / 20 °C

1.3: EtOH / 1,2-dichloro-ethane / 60 °C

2.1: 83 percent / O₂; CuCl; PdCl₂ / dimethylformamide; H₂O / 48 h / 20 °C

3.1: Jones' reagent / acetone / 0.5 h / 0 °C

With jones' reagent; dicobalt octacarbonyl; oxygen; copper(l) chloride; palladium dichloride; In dichloromethane; water; N,N-dimethyl-formamide; acetone; 2.1: Wacker oxidation;

DOI:10.1016/S0040-4020(02)00044-3

upstream raw materials:

2-((2S,3S,4R,4aR,5aR,9R,10aS,11aR)-2-Allyl-3,4-bis-benzyloxy-7-triethylsilanyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-yl)-ethanol

1-[(2S,3S,4R,4aR,5aR,9R,10aS,11aR)-3,4-Bis-benzyloxy-9-(2-hydroxy-ethyl)-7-triethylsilanyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl]-propan-2-one

methyl 2,3-di-O-benzyl-4,6-O-isopropylidene-α-D-glucopyranoside

methyl 6-deoxy-6-iodo-2,3-bis-O-(phenylmethyl)-α-D-glucopyranoside

Downstream raw materials:

(2S,3S,4R,4aR,5aR,8S,9R,10aS,11aR)-3,4-Bis-benzyloxy-2-(2-methyl-[1,3]dithian-2-ylmethyl)-9-prop-2-ynyl-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-ol

(2S,3S,4R,4aR,5aR,8R,9R,10aS,11aR)-3,4-Bis-benzyloxy-2-(2-methyl-[1,3]dithian-2-ylmethyl)-9-prop-2-ynyl-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-ol

C₄₀H₅₆O₇S₂Si

C₄₁H₅₆O₆S₂Si

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