(2S,3R,4R)-4-[(2S,3S,6S)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-3-methyl-tetrahydro-pyran-2-yl]-2-methyl-pentane-1,3-diol

Base Information

• Chemical Name: (2S,3R,4R)-4-[(2S,3S,6S)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-3-methyl-tetrahydro-pyran-2-yl]-2-methyl-pentane-1,3-diol
• CAS No.: 148338-54-9
• Molecular Formula: C₂₂H₃₆O₄
• Molecular Weight: 364.525

Synonyms:(2S,3R,4R)-4-[(2S,3S,6S)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-3-methyl-tetrahydro-pyran-2-yl]-2-methyl-pentane-1,3-diol

Chemical Property of (2S,3R,4R)-4-[(2S,3S,6S)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-3-methyl-tetrahydro-pyran-2-yl]-2-methyl-pentane-1,3-diol

Chemical Property:

Purity/Quality:

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Technology Process of (2S,3R,4R)-4-[(2S,3S,6S)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-3-methyl-tetrahydro-pyran-2-yl]-2-methyl-pentane-1,3-diol

There total 15 articles about (2S,3R,4R)-4-[(2S,3S,6S)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-3-methyl-tetrahydro-pyran-2-yl]-2-methyl-pentane-1,3-diol 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)-(2R,3S,6S)-1-Benzyloxy-2-methyl-6-(R)-oxiranyl-hept-4-en-3-ol → (2S,3R,4R)-4-[(2S,3S,6S)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-3-methyl-tetrahydro-pyran-2-yl]-2-methyl-pentane-1,3-diol (148338-54-9)

Guidance literature:

Multi-step reaction with 13 steps

1: H₂ / Pd/C / ethyl acetate

2: CSA / CH₂Cl₂

3: TPAP, NMO / CH₂Cl₂

4: tetrahydrofuran

5: TPAP, NMO / CH₂Cl₂

6: tetrahydrofuran / -78 °C

7: 87 percent / LiAlH₄ / tetrahydrofuran

8: KH / 1,2-dimethoxy-ethane

9: n-BuLi / tetrahydrofuran / -78 °C

10: 1) CF₃CO₂H, H₂O, 2) LiAlH₄ / 1) THF, 2) THF

11: NaIO₄ / acetone; H₂O

12: LiAlH₄ / tetrahydrofuran

13: 1) BH₃*THF, 2) H₂O₂, aq. NaOH / 1) 25 deg C

With sodium hydroxide; sodium periodate; lithium aluminium tetrahydride; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; borane-THF; camphor-10-sulfonic acid; water; hydrogen; dihydrogen peroxide; potassium hydride; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; water; ethyl acetate; acetone;

DOI:10.1016/S0040-4039(00)77501-0

Reference yield:

(E)-(3S,6S,7R)-8-Benzyloxy-2-(4-methoxy-benzyloxy)-6-methoxymethoxy-3,7-dimethyl-oct-4-en-1-ol → (2S,3R,4R)-4-[(2S,3S,6S)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-3-methyl-tetrahydro-pyran-2-yl]-2-methyl-pentane-1,3-diol (148338-54-9)

Guidance literature:

Multi-step reaction with 14 steps

2: H₂ / Pd/C / ethyl acetate

3: CSA / CH₂Cl₂

4: TPAP, NMO / CH₂Cl₂

5: tetrahydrofuran

6: TPAP, NMO / CH₂Cl₂

7: tetrahydrofuran / -78 °C

8: 87 percent / LiAlH₄ / tetrahydrofuran

9: KH / 1,2-dimethoxy-ethane

10: n-BuLi / tetrahydrofuran / -78 °C

11: 1) CF₃CO₂H, H₂O, 2) LiAlH₄ / 1) THF, 2) THF

12: NaIO₄ / acetone; H₂O

13: LiAlH₄ / tetrahydrofuran

14: 1) BH₃*THF, 2) H₂O₂, aq. NaOH / 1) 25 deg C

With sodium hydroxide; sodium periodate; lithium aluminium tetrahydride; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; borane-THF; camphor-10-sulfonic acid; water; hydrogen; dihydrogen peroxide; potassium hydride; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; water; ethyl acetate; acetone;

DOI:10.1016/S0040-4039(00)77501-0

Reference yield:

(E)-(3S,6S,7R)-8-Benzyloxy-2-(4-methoxy-benzyloxy)-6-methoxymethoxy-3,7-dimethyl-oct-4-enoic acid methyl ester → (2S,3R,4R)-4-[(2S,3S,6S)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-3-methyl-tetrahydro-pyran-2-yl]-2-methyl-pentane-1,3-diol (148338-54-9)

Guidance literature:

Multi-step reaction with 15 steps

1: LiAlH₄ / tetrahydrofuran / 0 - 25 °C

3: H₂ / Pd/C / ethyl acetate

4: CSA / CH₂Cl₂

5: TPAP, NMO / CH₂Cl₂

6: tetrahydrofuran

7: TPAP, NMO / CH₂Cl₂

8: tetrahydrofuran / -78 °C

9: 87 percent / LiAlH₄ / tetrahydrofuran

10: KH / 1,2-dimethoxy-ethane

11: n-BuLi / tetrahydrofuran / -78 °C

12: 1) CF₃CO₂H, H₂O, 2) LiAlH₄ / 1) THF, 2) THF

13: NaIO₄ / acetone; H₂O

14: LiAlH₄ / tetrahydrofuran

15: 1) BH₃*THF, 2) H₂O₂, aq. NaOH / 1) 25 deg C

With sodium hydroxide; sodium periodate; lithium aluminium tetrahydride; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; borane-THF; camphor-10-sulfonic acid; water; hydrogen; dihydrogen peroxide; potassium hydride; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; water; ethyl acetate; acetone;

DOI:10.1016/S0040-4039(00)77501-0

upstream raw materials:

(E)-(R)-4-[(2S,3S,6S)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-3-methyl-tetrahydro-pyran-2-yl]-2-methyl-pent-3-en-1-ol

[(2S,3S,6S)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-3-methyl-tetrahydro-pyran-2-yl]-methanol

(R)-2-[(2S,3S,6S)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-3-methyl-tetrahydro-pyran-2-yl]-pent-3-yn-2-ol

(E)-(R)-2-[(2S,3S,6S)-6-((R)-2-Benzyloxy-1-methyl-ethyl)-3-methyl-tetrahydro-pyran-2-yl]-pent-3-en-2-ol

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