ethyl tetrahydro-4(S)-hydroxy-5(R)-<((triphenylmethyl)oxy)methyl>-2(S)-furanacetate

Base Information

• Chemical Name: ethyl tetrahydro-4(S)-hydroxy-5(R)-<((triphenylmethyl)oxy)methyl>-2(S)-furanacetate
• CAS No.: 79356-73-3
• Molecular Formula: C₂₈H₃₀O₅
• Molecular Weight: 446.543

Synonyms:ethyl tetrahydro-4(S)-hydroxy-5(R)-<((triphenylmethyl)oxy)methyl>-2(S)-furanacetate

Chemical Property of ethyl tetrahydro-4(S)-hydroxy-5(R)-<((triphenylmethyl)oxy)methyl>-2(S)-furanacetate

Chemical Property:

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Technology Process of ethyl tetrahydro-4(S)-hydroxy-5(R)-<((triphenylmethyl)oxy)methyl>-2(S)-furanacetate

There total 15 articles about ethyl tetrahydro-4(S)-hydroxy-5(R)-<((triphenylmethyl)oxy)methyl>-2(S)-furanacetate 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: 80.0%

trityl chloride (76-83-5) + ethyl 2-[(4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]acetate (79308-52-4) → ((4S,5R)-4-Hydroxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-acetic acid ethyl ester (79308-56-8,79356-70-0,79356-73-3,79356-74-4,79356-77-7,79356-78-8) + ethyl tetrahydro-4(S)-hydroxy-5(R)-<((triphenylmethyl)oxy)methyl>-2(R)-furanacetate (79356-74-4)

Guidance literature:

With dmap; In pyridine; Yields of byproduct given;

DOI:10.1016/S0040-4039(01)90546-5

Reference yield: 67.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + (4S,5R)-5-((trityloxy)methyl)tetrahydrofuran-2,4-diol (124290-99-9) → ethyl tetrahydro-4(S)-hydroxy-5(R)-<((triphenylmethyl)oxy)methyl>-2(S)-furanacetate (79356-73-3) + ethyl tetrahydro-4(S)-hydroxy-5(R)-<((triphenylmethyl)oxy)methyl>-2(R)-furanacetate (79356-74-4)

Guidance literature:

diethoxyphosphoryl-acetic acid ethyl ester; With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 0.5h;

(4S,5R)-5-((trityloxy)methyl)tetrahydrofuran-2,4-diol; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1021/acs.joc.5b02595

Reference yield:

trityl chloride (76-83-5) + ethyl 2-[(4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]acetate (79308-52-4) → ethyl tetrahydro-4(S)-hydroxy-5(R)-<((triphenylmethyl)oxy)methyl>-2(S)-furanacetate (79356-73-3) + ethyl tetrahydro-4(S)-hydroxy-5(R)-<((triphenylmethyl)oxy)methyl>-2(R)-furanacetate (79356-74-4)

Guidance literature:

With dmap; In pyridine; Yield given. Yields of byproduct given;

DOI:10.1016/S0040-4039(01)90546-5

upstream raw materials:

((R)-4-Oxo-5-trityloxymethyl-tetrahydro-furan-2-yl)-acetic acid ethyl ester

2-deoxy-D-ribose

ethyl 2,3,4-trideoxy-D-ribo-hept-2-enoate

ethyl 2-[(4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]acetate

Downstream raw materials:

[(4R,5R)-4-Hydroxy-5-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-2-yl]-acetic acid ethyl ester

((R)-4-Oxo-5-trityloxymethyl-tetrahydro-furan-2-yl)-acetic acid ethyl ester

[(4S,5R)-4-(Toluene-4-sulfonyloxy)-5-trityloxymethyl-tetrahydro-furan-2-yl]-acetic acid ethyl ester

[(4S,5R)-5-Hydroxymethyl-4-(toluene-4-sulfonyloxy)-tetrahydro-furan-2-yl]-acetic acid ethyl ester

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