(4R,5R)-5-((R)-1-tert-Butoxycarbonylamino-2-trityloxy-ethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid methyl ester

Base Information

Chemical Name:(4R,5R)-5-((R)-1-tert-Butoxycarbonylamino-2-trityloxy-ethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid methyl ester
CAS No.:212892-08-5
Molecular Formula:C₃₃H₃₉NO₇
Molecular Weight:561.675
Hs Code.:

Synonyms:(4R,5R)-5-((R)-1-tert-Butoxycarbonylamino-2-trityloxy-ethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid methyl ester

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Chemical Property of (4R,5R)-5-((R)-1-tert-Butoxycarbonylamino-2-trityloxy-ethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid methyl ester

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Technology Process of (4R,5R)-5-((R)-1-tert-Butoxycarbonylamino-2-trityloxy-ethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid methyl ester

There total 1 articles about (4R,5R)-5-((R)-1-tert-Butoxycarbonylamino-2-trityloxy-ethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic 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: 90.0%

: 67-56-1
methanol

: 124665-84-5
(3R,4R,5R)-1-(tert-butoxycarbonyl)-3,4-isopropylidenedioxy-5-trityloxymethyl-2-pyrrolidinone

: 212892-08-5
(4R,5R)-5-((R)-1-tert-Butoxycarbonylamino-2-trityloxy-ethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid methyl ester

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; for 2h; Ambient temperature;
DOI:10.1016/S0040-4020(98)00542-0

Reference yield: 88.0%

: 212892-08-5
(4R,5R)-5-((R)-1-tert-Butoxycarbonylamino-2-trityloxy-ethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid methyl ester

: 212963-42-3
[(R)-1-((4R,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-trityloxy-ethyl]-carbamic acid tert-butyl ester

Guidance literature:: With sodium tetrahydroborate; In ethanol; for 8h; Ambient temperature;
DOI:10.1016/S0040-4020(98)00542-0

Reference yield:

: 212892-08-5
(4R,5R)-5-((R)-1-tert-Butoxycarbonylamino-2-trityloxy-ethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid methyl ester

: (3aS,4S,6R,6aR)-4-((S)-1-Methoxymethoxy-but-3-enyl)-2,2-dimethyl-6-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole

Guidance literature:: Multi-step reaction with 9 steps

1: 88 percent / NaBH₄ / ethanol / 8 h / Ambient temperature

2: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -20 deg C, 15 min, 2.) CH₂Cl₂, -20 deg C to rt

3: 401 mg / tetrahydrofuran / 0.5 h / -78 °C

4: 88 percent / MsCl, Et₃N / CH₂Cl₂ / 1 h / 0 °C

5: 1.) O₃, 2.) NaBH₄ / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, EtOH, 0 deg C

7: N,N-diethylaniline / CH₂Cl₂ / 40 h / Ambient temperature

8: 2,6-lutidine / CH₂Cl₂ / 3 h / Ambient temperature

9: TBAF / tetrahydrofuran / 0.5 h / Ambient temperature

With 2,6-dimethylpyridine; sodium tetrahydroborate; oxalyl dichloride; tetrabutyl ammonium fluoride; ozone; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; N,N-diethylaniline; In tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1016/S0040-4020(98)00542-0