(2R,3S)-4-[(2R,4S,5S,6S)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-4,6-dimethoxy-5-triethylsilanyloxy-tetrahydro-pyran-2-yl]-3-methoxy-2-methoxymethoxy-butyric acid methyl ester

Base Information

Chemical Name:(2R,3S)-4-[(2R,4S,5S,6S)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-4,6-dimethoxy-5-triethylsilanyloxy-tetrahydro-pyran-2-yl]-3-methoxy-2-methoxymethoxy-butyric acid methyl ester
CAS No.:566927-66-0
Molecular Formula:C₃₂H₅₆O₁₀Si
Molecular Weight:628.876
Hs Code.:

(2R,3S)-4-[(2R,4S,5S,6S)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-4,6-dimethoxy-5-triethylsilanyloxy-tetrahydro-pyran-2-yl]-3-methoxy-2-methoxymethoxy-butyric acid methyl ester

Synonyms:(2R,3S)-4-[(2R,4S,5S,6S)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-4,6-dimethoxy-5-triethylsilanyloxy-tetrahydro-pyran-2-yl]-3-methoxy-2-methoxymethoxy-butyric acid methyl ester

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Chemical Property of (2R,3S)-4-[(2R,4S,5S,6S)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-4,6-dimethoxy-5-triethylsilanyloxy-tetrahydro-pyran-2-yl]-3-methoxy-2-methoxymethoxy-butyric acid methyl ester

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Technology Process of (2R,3S)-4-[(2R,4S,5S,6S)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-4,6-dimethoxy-5-triethylsilanyloxy-tetrahydro-pyran-2-yl]-3-methoxy-2-methoxymethoxy-butyric acid methyl ester

There total 18 articles about (2R,3S)-4-[(2R,4S,5S,6S)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-4,6-dimethoxy-5-triethylsilanyloxy-tetrahydro-pyran-2-yl]-3-methoxy-2-methoxymethoxy-butyric 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: 80.0%

: 513-35-9
2-methyl-but-2-ene

: 24153-51-3,175791-16-9,353495-36-0,6843-83-0
diazomethane

: 566927-65-9
[(2S,3S,4S,6R)-2-(2-Benzyloxy-1,1-dimethyl-ethyl)-2,4-dimethoxy-6-((2S,3S)-2-methoxy-3-methoxymethoxy-pent-4-enyl)-tetrahydro-pyran-3-yloxy]-triethyl-silane

: 566927-66-0
(2R,3S)-4-[(2R,4S,5S,6S)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-4,6-dimethoxy-5-triethylsilanyloxy-tetrahydro-pyran-2-yl]-3-methoxy-2-methoxymethoxy-butyric acid methyl ester

Guidance literature:: [(2S,3S,4S,6R)-2-(2-Benzyloxy-1,1-dimethyl-ethyl)-2,4-dimethoxy-6-((2S,3S)-2-methoxy-3-methoxymethoxy-pent-4-enyl)-tetrahydro-pyran-3-yloxy]-triethyl-silane; With 4-methylmorpholine N-oxide; osmium(VIII) oxide; In water; acetone;

With pyridine; lead(IV) tetraacetate; In dichloromethane;

2-methyl-but-2-ene; diazomethane; With sodium chlorite; sodium dihydrogenphosphate; more than 3 stages;

Reference yield:

: 61674-96-2
4-(benzyloxy)-3,3-dimethylbutan-2-one

: 566927-66-0
(2R,3S)-4-[(2R,4S,5S,6S)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-4,6-dimethoxy-5-triethylsilanyloxy-tetrahydro-pyran-2-yl]-3-methoxy-2-methoxymethoxy-butyric acid methyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: LDA / tetrahydrofuran / -78 °C

1.2: 94 percent / tetrahydrofuran / -78 °C

2.1: 81 percent Turnov_. / Dess-Martin periodinane / CH₂Cl₂ / -10 °C

3.1: 92 percent / PTSA / toluene / 20 °C

4.1: NaBH₄; CeCl₃*7H₂O / methanol / -30 °C

5.1: mCPBA; NaHCO₃ / CH₂Cl₂ / 0 °C

6.1: t-BuOK / tetrahydrofuran / 0 °C

7.1: 2,6-lutidine / CH₂Cl₂

8.1: OsO₄; NMO; H₂O / acetone

8.2: Pb(OAc)4; pyridine / CH₂Cl₂

9.1: NaClO₂; NaH₂PO₄; 2-Me-2-butene / H₂O; 2-methyl-propan-2-ol

10.1: diethyl ether / 0 °C

With 2,6-dimethylpyridine; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; osmium(VIII) oxide; N-methyl-2-indolinone; cerium(III) chloride; 2-methyl-but-2-ene; potassium tert-butylate; water; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone; toluene; tert-butyl alcohol; 2.1: Dess-Martin oxidation / 4.1: Luche reduction;
DOI:10.1002/anie.200351145

Reference yield:

: 325172-29-0
(3R)-1-[(4-methoxybenzyl)oxy]hex-5-en-3-ol

: 566927-66-0
(2R,3S)-4-[(2R,4S,5S,6S)-6-(2-Benzyloxy-1,1-dimethyl-ethyl)-4,6-dimethoxy-5-triethylsilanyloxy-tetrahydro-pyran-2-yl]-3-methoxy-2-methoxymethoxy-butyric acid methyl ester

Guidance literature:: Multi-step reaction with 16 steps

1.1: 97 percent / 2,6-lutidine / CH₂Cl₂

2.1: OsO₄; NMO; H₂O / acetone

2.2: 80 percent / Pb(OAc)4; pyridine / CH₂Cl₂

3.1: sBuLi; (+)-Ipc₂BOMe / tetrahydrofuran / -78 - 0 °C

3.2: tetrahydrofuran / -95 - 20 °C

3.3: 91 percent / 30 percent H₂O₂; NaOH / tetrahydrofuran / 16 h

4.1: 89 percent / NaH / dimethylformamide / -5 °C

5.1: 88 percent / DDQ / CH₂Cl₂; H₂O / 0 °C

6.1: 87 percent / py*SO₃; Et₃N / dimethylsulfoxide; CH₂Cl₂ / 0 °C

7.1: LDA / tetrahydrofuran / -78 °C

7.2: 94 percent / tetrahydrofuran / -78 °C

8.1: 81 percent Turnov_. / Dess-Martin periodinane / CH₂Cl₂ / -10 °C

9.1: 92 percent / PTSA / toluene / 20 °C

10.1: NaBH₄; CeCl₃*7H₂O / methanol / -30 °C

11.1: mCPBA; NaHCO₃ / CH₂Cl₂ / 0 °C

12.1: t-BuOK / tetrahydrofuran / 0 °C

13.1: 2,6-lutidine / CH₂Cl₂

14.1: OsO₄; NMO; H₂O / acetone

14.2: Pb(OAc)4; pyridine / CH₂Cl₂

15.1: NaClO₂; NaH₂PO₄; 2-Me-2-butene / H₂O; 2-methyl-propan-2-ol

16.1: diethyl ether / 0 °C

With 2,6-dimethylpyridine; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; osmium(VIII) oxide; N-methyl-2-indolinone; cerium(III) chloride; 2-methyl-but-2-ene; potassium tert-butylate; water; sec.-butyllithium; sulfur trioxide pyridine complex; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; (+)-B-methoxydiisocamphenylborane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; 8.1: Dess-Martin oxidation / 10.1: Luche reduction;
DOI:10.1002/anie.200351145