(2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5S,6S)-6-(2-Azido-ethyl)-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy]-3-hydroxy-4,5-dimethoxy-tetrahydro-pyran-2-carboxylic acid benzyl ester

Base Information

Chemical Name:(2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5S,6S)-6-(2-Azido-ethyl)-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy]-3-hydroxy-4,5-dimethoxy-tetrahydro-pyran-2-carboxylic acid benzyl ester
CAS No.:511511-46-9
Molecular Formula:C₃₂H₄₃N₃O₁₁
Molecular Weight:645.707
Hs Code.:

(2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5S,6S)-6-(2-Azido-ethyl)-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy]-3-hydroxy-4,5-dimethoxy-tetrahydro-pyran-2-carboxylic acid benzyl ester

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Chemical Property of (2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5S,6S)-6-(2-Azido-ethyl)-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy]-3-hydroxy-4,5-dimethoxy-tetrahydro-pyran-2-carboxylic acid benzyl ester

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Technology Process of (2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5S,6S)-6-(2-Azido-ethyl)-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy]-3-hydroxy-4,5-dimethoxy-tetrahydro-pyran-2-carboxylic acid benzyl ester

There total 12 articles about (2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5S,6S)-6-(2-Azido-ethyl)-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy]-3-hydroxy-4,5-dimethoxy-tetrahydro-pyran-2-carboxylic acid benzyl 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:

: 511511-29-8
(2R,3R,4S,5S,6S)-6-(2-Azido-ethyl)-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-ol

: 511511-46-9
(2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5S,6S)-6-(2-Azido-ethyl)-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy]-3-hydroxy-4,5-dimethoxy-tetrahydro-pyran-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 88 percent / N-iodosuccinimide; mol. sieves 4 Angstroem; TfOH / toluene; dioxane; CH₂Cl₂ / 0.5 h / -20 °C

2: KOtBu / methanol; dioxane / 3 h

3: pTsOH / dimethylformamide / 1 h

4: NaH / dimethylformamide / 0.5 h / 0 °C

5: AcOH / H₂O / 1 h / 60 °C

6: potassium bromide; tetrabutylammonium chloride; NaHCO₃ / NaOCl; 2,2,6,6-tetramethylpiperidin-1-oxyl / CH₂Cl₂; H₂O / 1 h / 0 °C

7: KHCO₃ / dimethylformamide / 2 h

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; potassium tert-butylate; tetrabutyl-ammonium chloride; sodium hydride; sodium hydrogencarbonate; potassium hydrogencarbonate; toluene-4-sulfonic acid; acetic acid; potassium bromide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; In 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 2: Zemplen deacetylation;
DOI:10.1002/1099-0690(200212)2002:23<3954::AID-EJOC3954>3.0.CO;2-2

Reference yield:

: [(2S,3S,4R,5R,6R)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-6-methoxymethyl-tetrahydro-pyran-2-yl]-acetaldehyde

: 511511-46-9
(2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5S,6S)-6-(2-Azido-ethyl)-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy]-3-hydroxy-4,5-dimethoxy-tetrahydro-pyran-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 0.952 g / LiAlH₄ / tetrahydrofuran / 0.5 h

2: pyridine / CH₂Cl₂ / 16 h

3: NaN₃ / dimethylformamide / 3 h / 60 °C

4: 86 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h

5: 88 percent / N-iodosuccinimide; mol. sieves 4 Angstroem; TfOH / toluene; dioxane; CH₂Cl₂ / 0.5 h / -20 °C

6: KOtBu / methanol; dioxane / 3 h

7: pTsOH / dimethylformamide / 1 h

8: NaH / dimethylformamide / 0.5 h / 0 °C

9: AcOH / H₂O / 1 h / 60 °C

10: potassium bromide; tetrabutylammonium chloride; NaHCO₃ / NaOCl; 2,2,6,6-tetramethylpiperidin-1-oxyl / CH₂Cl₂; H₂O / 1 h / 0 °C

11: KHCO₃ / dimethylformamide / 2 h

With pyridine; N-iodo-succinimide; lithium aluminium tetrahydride; sodium azide; trifluorormethanesulfonic acid; 4 A molecular sieve; potassium tert-butylate; tetrabutyl ammonium fluoride; tetrabutyl-ammonium chloride; sodium hydride; sodium hydrogencarbonate; potassium hydrogencarbonate; toluene-4-sulfonic acid; acetic acid; potassium bromide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 6: Zemplen deacetylation;
DOI:10.1002/1099-0690(200212)2002:23<3954::AID-EJOC3954>3.0.CO;2-2

Reference yield:

: 511511-36-7
((2R,3R,4R,5S,6S)-6-Allyl-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

: 511511-46-9
(2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5S,6S)-6-(2-Azido-ethyl)-4-benzyloxy-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy]-3-hydroxy-4,5-dimethoxy-tetrahydro-pyran-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 12 steps

1.1: O₃ / CH₂Cl₂; methanol / 2 h / -70 °C

1.2: dimethyl sulfide / methanol; CH₂Cl₂ / 16 h / -50 - 20 °C

2.1: 0.952 g / LiAlH₄ / tetrahydrofuran / 0.5 h

3.1: pyridine / CH₂Cl₂ / 16 h

4.1: NaN₃ / dimethylformamide / 3 h / 60 °C

5.1: 86 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h

6.1: 88 percent / N-iodosuccinimide; mol. sieves 4 Angstroem; TfOH / toluene; dioxane; CH₂Cl₂ / 0.5 h / -20 °C

7.1: KOtBu / methanol; dioxane / 3 h

8.1: pTsOH / dimethylformamide / 1 h

9.1: NaH / dimethylformamide / 0.5 h / 0 °C

10.1: AcOH / H₂O / 1 h / 60 °C

11.1: potassium bromide; tetrabutylammonium chloride; NaHCO₃ / NaOCl; 2,2,6,6-tetramethylpiperidin-1-oxyl / CH₂Cl₂; H₂O / 1 h / 0 °C

12.1: KHCO₃ / dimethylformamide / 2 h

With pyridine; N-iodo-succinimide; lithium aluminium tetrahydride; sodium azide; trifluorormethanesulfonic acid; 4 A molecular sieve; potassium tert-butylate; tetrabutyl ammonium fluoride; tetrabutyl-ammonium chloride; sodium hydride; sodium hydrogencarbonate; potassium hydrogencarbonate; toluene-4-sulfonic acid; ozone; acetic acid; potassium bromide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 7.1: Zemplen deacetylation;
DOI:10.1002/1099-0690(200212)2002:23<3954::AID-EJOC3954>3.0.CO;2-2