(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-(1-ethoxy-ethoxymethyl)-tetrahydro-pyran-3-ol

Base Information

• Chemical Name: (2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-(1-ethoxy-ethoxymethyl)-tetrahydro-pyran-3-ol
• CAS No.: 474248-51-6
• Molecular Formula: C₂₅H₃₄O₆
• Molecular Weight: 430.541

Synonyms:(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-(1-ethoxy-ethoxymethyl)-tetrahydro-pyran-3-ol

Chemical Property of (2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-(1-ethoxy-ethoxymethyl)-tetrahydro-pyran-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-(1-ethoxy-ethoxymethyl)-tetrahydro-pyran-3-ol

There total 14 articles about (2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-(1-ethoxy-ethoxymethyl)-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:

(E)-ethyl 4-((2R,4S,5R)-5-hydroxy-2-(4-methoxyphenyl)-1,3-dioxan-4-yl)but-2-enoate (602301-70-2) → (2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-(1-ethoxy-ethoxymethyl)-tetrahydro-pyran-3-ol (474248-51-6)

Guidance literature:

Multi-step reaction with 14 steps

1.1: imidazole / dimethylformamide

2.1: DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

3.1: 139.35 g / diethyl-D-tartrate; molecular sieves 4 Angstroem; t-butylhydroperoxide / titanium(IV) tetraisopropoxide / CH₂Cl₂ / 27 h / -30 °C

4.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 °C

5.1: 30 g / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.33 h / 0 °C

6.1: TBAF / tetrahydrofuran / 0.5 h / 20 °C

7.1: 15.8 g / PPTS / CH₂Cl₂ / 3 h / 0 °C

8.1: O₃ / CH₂Cl₂; methanol / -78 °C

8.2: NaBH₄ / CH₂Cl₂; methanol / 20 °C

9.1: 5.63 g / NaH / tetrahydrofuran; dimethylformamide / 13 h / 20 °C

10.1: CSA / methanol; CH₂Cl₂ / 1.2 h

11.1: imidazole / dimethylformamide / 3 h / 20 °C

12.1: 2.90 g / CSA / methanol / 0.33 h / 0 °C

13.1: PPTS / CH₂Cl₂ / 1 h

14.1: 88.2 mg / TBAF / tetrahydrofuran / 3 h

With 1H-imidazole; tert.-butylhydroperoxide; oxalyl dichloride; diethyl (2S,3S)-tartrate; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; ozone; dimethyl sulfoxide; triethylamine; titanium(IV) isopropylate; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; 3.1: Sharpless asymmetric epoxidation / 4.1: Swern oxidation / 5.1: Wittig reaction;

DOI:10.1016/S0040-4020(03)00913-X

Reference yield:

(E)-4-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-but-2-en-1-ol (602301-72-4) → (2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-(1-ethoxy-ethoxymethyl)-tetrahydro-pyran-3-ol (474248-51-6)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 139.35 g / diethyl-D-tartrate; molecular sieves 4 Angstroem; t-butylhydroperoxide / titanium(IV) tetraisopropoxide / CH₂Cl₂ / 27 h / -30 °C

2.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 °C

3.1: 30 g / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.33 h / 0 °C

4.1: TBAF / tetrahydrofuran / 0.5 h / 20 °C

5.1: 15.8 g / PPTS / CH₂Cl₂ / 3 h / 0 °C

6.1: O₃ / CH₂Cl₂; methanol / -78 °C

6.2: NaBH₄ / CH₂Cl₂; methanol / 20 °C

7.1: 5.63 g / NaH / tetrahydrofuran; dimethylformamide / 13 h / 20 °C

8.1: CSA / methanol; CH₂Cl₂ / 1.2 h

9.1: imidazole / dimethylformamide / 3 h / 20 °C

10.1: 2.90 g / CSA / methanol / 0.33 h / 0 °C

11.1: PPTS / CH₂Cl₂ / 1 h

12.1: 88.2 mg / TBAF / tetrahydrofuran / 3 h

With 1H-imidazole; tert.-butylhydroperoxide; oxalyl dichloride; diethyl (2S,3S)-tartrate; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; sodium hydride; ozone; dimethyl sulfoxide; triethylamine; titanium(IV) isopropylate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Sharpless asymmetric epoxidation / 2.1: Swern oxidation / 3.1: Wittig reaction;

DOI:10.1016/S0040-4020(03)00913-X

Reference yield:

(E)-4-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-but-2-enoic acid ethyl ester (602301-71-3) → (2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-(1-ethoxy-ethoxymethyl)-tetrahydro-pyran-3-ol (474248-51-6)

Guidance literature:

Multi-step reaction with 13 steps

1.1: DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

2.1: 139.35 g / diethyl-D-tartrate; molecular sieves 4 Angstroem; t-butylhydroperoxide / titanium(IV) tetraisopropoxide / CH₂Cl₂ / 27 h / -30 °C

3.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 °C

4.1: 30 g / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.33 h / 0 °C

5.1: TBAF / tetrahydrofuran / 0.5 h / 20 °C

6.1: 15.8 g / PPTS / CH₂Cl₂ / 3 h / 0 °C

7.1: O₃ / CH₂Cl₂; methanol / -78 °C

7.2: NaBH₄ / CH₂Cl₂; methanol / 20 °C

8.1: 5.63 g / NaH / tetrahydrofuran; dimethylformamide / 13 h / 20 °C

9.1: CSA / methanol; CH₂Cl₂ / 1.2 h

10.1: imidazole / dimethylformamide / 3 h / 20 °C

11.1: 2.90 g / CSA / methanol / 0.33 h / 0 °C

12.1: PPTS / CH₂Cl₂ / 1 h

13.1: 88.2 mg / TBAF / tetrahydrofuran / 3 h

With 1H-imidazole; tert.-butylhydroperoxide; oxalyl dichloride; diethyl (2S,3S)-tartrate; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; ozone; dimethyl sulfoxide; triethylamine; titanium(IV) isopropylate; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; 2.1: Sharpless asymmetric epoxidation / 3.1: Swern oxidation / 4.1: Wittig reaction;

DOI:10.1016/S0040-4020(03)00913-X

upstream raw materials:

(2R,4aR,6S,7R,8aS)-2-(4-Methoxy-phenyl)-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

(2R,4aR,6S,7R,8aS)-6-Hydroxymethyl-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

(E)-ethyl 4-((2R,4S,5R)-5-hydroxy-2-(4-methoxyphenyl)-1,3-dioxan-4-yl)but-2-enoate

(2R,3S,5R,6S)-5-(benzyloxy)-6-((benzyloxy)methyl)-2-(hydroxymethyl)tetrahydro-2H-pyran-3-ol

Downstream raw materials:

[(2R,4aR,6S,7R,8aS)-6-{3-[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-(1-ethoxy-ethoxymethyl)-tetrahydro-pyran-3-yloxy]-3-phenylsulfanyl-propyl}-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-tert-butyl-dimethyl-silane

(2R,4aR,5aS,8R,9S,10aR,11aS)-8-((2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-vinyl-tetrahydro-pyran-3-yloxy)-2-(4-methoxy-phenyl)-9-vinyl-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene

(2R,4aR,5aS,8R,9S,10aR,11aS)-9-Allyl-8-((2R,3S,5R,6S)-5-benzyloxy-6-benzyloxymethyl-2-vinyl-tetrahydro-pyran-3-yloxy)-2-(4-methoxy-phenyl)-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene

(2R,4aR,5aS,8R,9S,10aR,11aS)-8-((2R,3S,5R,6S)-2-Allyl-5-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-2-(4-methoxy-phenyl)-9-vinyl-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene

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