(2R,3S,4R,6R)-2-[(2S,4S,5R,6S)-4-Benzyloxy-6-(2-hydroxy-ethyl)-5-methyl-tetrahydro-pyran-2-ylmethyl]-2-methoxy-6-[(R)-2-(4-methoxy-benzyloxy)-1,1-dimethyl-but-3-enyl]-4-methyl-tetrahydro-pyran-3-ol

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Chemical Name:(2R,3S,4R,6R)-2-[(2S,4S,5R,6S)-4-Benzyloxy-6-(2-hydroxy-ethyl)-5-methyl-tetrahydro-pyran-2-ylmethyl]-2-methoxy-6-[(R)-2-(4-methoxy-benzyloxy)-1,1-dimethyl-but-3-enyl]-4-methyl-tetrahydro-pyran-3-ol
CAS No.:215120-34-6
Molecular Formula:C₃₇H₅₄O₈
Molecular Weight:626.831
Hs Code.:

(2R,3S,4R,6R)-2-[(2S,4S,5R,6S)-4-Benzyloxy-6-(2-hydroxy-ethyl)-5-methyl-tetrahydro-pyran-2-ylmethyl]-2-methoxy-6-[(R)-2-(4-methoxy-benzyloxy)-1,1-dimethyl-but-3-enyl]-4-methyl-tetrahydro-pyran-3-ol

Synonyms:(2R,3S,4R,6R)-2-[(2S,4S,5R,6S)-4-Benzyloxy-6-(2-hydroxy-ethyl)-5-methyl-tetrahydro-pyran-2-ylmethyl]-2-methoxy-6-[(R)-2-(4-methoxy-benzyloxy)-1,1-dimethyl-but-3-enyl]-4-methyl-tetrahydro-pyran-3-ol

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Chemical Property of (2R,3S,4R,6R)-2-[(2S,4S,5R,6S)-4-Benzyloxy-6-(2-hydroxy-ethyl)-5-methyl-tetrahydro-pyran-2-ylmethyl]-2-methoxy-6-[(R)-2-(4-methoxy-benzyloxy)-1,1-dimethyl-but-3-enyl]-4-methyl-tetrahydro-pyran-3-ol

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Technology Process of (2R,3S,4R,6R)-2-[(2S,4S,5R,6S)-4-Benzyloxy-6-(2-hydroxy-ethyl)-5-methyl-tetrahydro-pyran-2-ylmethyl]-2-methoxy-6-[(R)-2-(4-methoxy-benzyloxy)-1,1-dimethyl-but-3-enyl]-4-methyl-tetrahydro-pyran-3-ol

There total 10 articles about (2R,3S,4R,6R)-2-[(2S,4S,5R,6S)-4-Benzyloxy-6-(2-hydroxy-ethyl)-5-methyl-tetrahydro-pyran-2-ylmethyl]-2-methoxy-6-[(R)-2-(4-methoxy-benzyloxy)-1,1-dimethyl-but-3-enyl]-4-methyl-tetrahydro-pyran-3-ol 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: 65.0%

: 215120-33-5
(Z)-(3S,4R,6R,8R)-1-{(2S,4S,5R,6S)-4-Benzyloxy-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-pyran-2-yl}-6-(tert-butyl-dimethyl-silanyloxy)-2-ethylsulfanyl-8-(4-methoxy-benzyloxy)-4,7,7-trimethyl-deca-1,9-dien-3-ol

: 149-73-5
trimethyl orthoformate

: 215120-34-6
(2R,3S,4R,6R)-2-[(2S,4S,5R,6S)-4-Benzyloxy-6-(2-hydroxy-ethyl)-5-methyl-tetrahydro-pyran-2-ylmethyl]-2-methoxy-6-[(R)-2-(4-methoxy-benzyloxy)-1,1-dimethyl-but-3-enyl]-4-methyl-tetrahydro-pyran-3-ol

Guidance literature:: With methanol; toluene-4-sulfonic acid; at 25 ℃; for 72h;
DOI:10.1021/ja982431b

Reference yield: 50.0%

: 215176-93-5
(4R,6R,8R)-1-{(2S,4S,5R,6S)-4-Benzyloxy-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-pyran-2-yl}-6-(tert-butyl-dimethyl-silanyloxy)-2-ethanesulfinyl-2-ethylsulfanyl-8-(4-methoxy-benzyloxy)-4,7,7-trimethyl-dec-9-en-3-ol

: 149-73-5
trimethyl orthoformate

: 215120-35-7
(2R,3R,4R,6R)-2-[(2S,4S,5R,6S)-4-Benzyloxy-6-(2-hydroxy-ethyl)-5-methyl-tetrahydro-pyran-2-ylmethyl]-2-methoxy-6-[(R)-2-(4-methoxy-benzyloxy)-1,1-dimethyl-but-3-enyl]-4-methyl-tetrahydro-pyran-3-ol

: 215120-34-6
(2R,3S,4R,6R)-2-[(2S,4S,5R,6S)-4-Benzyloxy-6-(2-hydroxy-ethyl)-5-methyl-tetrahydro-pyran-2-ylmethyl]-2-methoxy-6-[(R)-2-(4-methoxy-benzyloxy)-1,1-dimethyl-but-3-enyl]-4-methyl-tetrahydro-pyran-3-ol

Guidance literature:: With methanol; toluene-4-sulfonic acid; at 25 ℃; for 21h;
DOI:10.1021/ja982431b

Reference yield:

: 162718-31-2
((2S,3R,4S,6S)-4-Benzyloxy-6-hydroxymethyl-3-methyl-tetrahydro-pyran-2-yl)-acetic acid methyl ester

: 215120-34-6
(2R,3S,4R,6R)-2-[(2S,4S,5R,6S)-4-Benzyloxy-6-(2-hydroxy-ethyl)-5-methyl-tetrahydro-pyran-2-ylmethyl]-2-methoxy-6-[(R)-2-(4-methoxy-benzyloxy)-1,1-dimethyl-but-3-enyl]-4-methyl-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 9 steps

1: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) CH₂Cl₂, from -78 deg C to 0 deg C

2: tetrahydrofuran / a) -78 deg C, 5 min, b) 20 deg C, 16 h

3: 92 percent / aq. TFA / tetrahydrofuran / 4.5 h / 20 °C

4: ZnI₂ / CH₂Cl₂ / 5.5 h / 20 °C

5: LiAlH₄ / tetrahydrofuran / 0 °C

6: imidazole / dimethylformamide / 0 °C

7: 93 percent / m-CPBA / CH₂Cl₂ / -60 °C

8: 1.) LDA / 1.) THF, -78 deg C, 10 min, 2.) THF, -78 deg C, 30 min

9: 65 percent / p-TsOH*H₂O, MeOH / 72 h / 25 °C

With 1H-imidazole; methanol; lithium aluminium tetrahydride; oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; zinc(II) iodide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja982431b