(3R,4R,5R)-3,4-Bis-benzyloxy-5-hydroxy-hexanoic acid (2R,3R,4R,6S)-3-hydroxy-6-methoxy-2,4-dimethyl-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: (3R,4R,5R)-3,4-Bis-benzyloxy-5-hydroxy-hexanoic acid (2R,3R,4R,6S)-3-hydroxy-6-methoxy-2,4-dimethyl-tetrahydro-pyran-4-yl ester
• CAS No.: 110906-74-6
• Molecular Formula: C₂₈H₃₈O₈
• Molecular Weight: 502.605
• Mol file: 110906-74-6.mol

Synonyms:(3R,4R,5R)-3,4-Bis-benzyloxy-5-hydroxy-hexanoic acid (2R,3R,4R,6S)-3-hydroxy-6-methoxy-2,4-dimethyl-tetrahydro-pyran-4-yl ester

Chemical Property of (3R,4R,5R)-3,4-Bis-benzyloxy-5-hydroxy-hexanoic acid (2R,3R,4R,6S)-3-hydroxy-6-methoxy-2,4-dimethyl-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R,5R)-3,4-Bis-benzyloxy-5-hydroxy-hexanoic acid (2R,3R,4R,6S)-3-hydroxy-6-methoxy-2,4-dimethyl-tetrahydro-pyran-4-yl ester

There total 18 articles about (3R,4R,5R)-3,4-Bis-benzyloxy-5-hydroxy-hexanoic acid (2R,3R,4R,6S)-3-hydroxy-6-methoxy-2,4-dimethyl-tetrahydro-pyran-4-yl 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:

(2R,4aR,6S,8aS)-6-Methoxy-8-methylene-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine (72244-36-1) → (3R,4R,5R)-3,4-Bis-benzyloxy-5-hydroxy-hexanoic acid (2R,3R,4R,6S)-3-hydroxy-6-methoxy-2,4-dimethyl-tetrahydro-pyran-4-yl ester (110906-74-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) Hg(OAc)2 2.) NaBH₄ / 1.) THF-water, 20 deg C, 30 min 2.) aq. NaOH, 20 deg C, 5 min

2: 95 percent / N-bromosuccinimide, BaCO₃ / CCl₄ / 6 h / Heating

3: 84 percent / LiAlH₄ / tetrahydrofuran / 6 h / Heating

4: 2.) sym-collidine / 2.) CH₃CN, 0 deg C, 1 h

5: 98 percent / NaIO₄ / methanol; H₂O / 1 h / 20 °C

6: 33 percent / toluene-vinyl acetate-di-isopropylamine / 2 h / 120 °C / sealed system

7: TsOH, H₂O / dioxane

With 2,4,6-trimethyl-pyridine; sodium tetrahydroborate; sodium periodate; N-Bromosuccinimide; lithium aluminium tetrahydride; vinyl acetate; mercury(II) diacetate; water; toluene-4-sulfonic acid; diisopropylamine; toluene; barium carbonate; In tetrahydrofuran; 1,4-dioxane; methanol; tetrachloromethane; water;

DOI:10.1016/S0040-4039(00)95922-7

Reference yield:

Benzoic acid (2S,3R,6S)-2-bromomethyl-4-hydroxy-6-methoxy-4-methyl-tetrahydro-pyran-3-yl ester (26706-32-1,68536-35-6,74995-84-9) → (3R,4R,5R)-3,4-Bis-benzyloxy-5-hydroxy-hexanoic acid (2R,3R,4R,6S)-3-hydroxy-6-methoxy-2,4-dimethyl-tetrahydro-pyran-4-yl ester (110906-74-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 84 percent / LiAlH₄ / tetrahydrofuran / 6 h / Heating

2: 2.) sym-collidine / 2.) CH₃CN, 0 deg C, 1 h

3: 98 percent / NaIO₄ / methanol; H₂O / 1 h / 20 °C

4: 33 percent / toluene-vinyl acetate-di-isopropylamine / 2 h / 120 °C / sealed system

5: TsOH, H₂O / dioxane

With 2,4,6-trimethyl-pyridine; sodium periodate; lithium aluminium tetrahydride; vinyl acetate; water; toluene-4-sulfonic acid; diisopropylamine; toluene; In tetrahydrofuran; 1,4-dioxane; methanol; water;

DOI:10.1016/S0040-4039(00)95922-7

Reference yield:

methyl 4,6-O-(R)-benzylidene-2-deoxy-α-D-erythrohexopyranosid-3-ulose (63598-31-2) → (3R,4R,5R)-3,4-Bis-benzyloxy-5-hydroxy-hexanoic acid (2R,3R,4R,6S)-3-hydroxy-6-methoxy-2,4-dimethyl-tetrahydro-pyran-4-yl ester (110906-74-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 75 percent / NaNH₂ / tetrahydrofuran / 0.25 h / 20 °C

2: 1.) Hg(OAc)2 2.) NaBH₄ / 1.) THF-water, 20 deg C, 30 min 2.) aq. NaOH, 20 deg C, 5 min

3: 95 percent / N-bromosuccinimide, BaCO₃ / CCl₄ / 6 h / Heating

4: 84 percent / LiAlH₄ / tetrahydrofuran / 6 h / Heating

5: 2.) sym-collidine / 2.) CH₃CN, 0 deg C, 1 h

6: 98 percent / NaIO₄ / methanol; H₂O / 1 h / 20 °C

7: 33 percent / toluene-vinyl acetate-di-isopropylamine / 2 h / 120 °C / sealed system

8: TsOH, H₂O / dioxane

With 2,4,6-trimethyl-pyridine; sodium tetrahydroborate; sodium periodate; N-Bromosuccinimide; lithium aluminium tetrahydride; vinyl acetate; mercury(II) diacetate; water; toluene-4-sulfonic acid; sodium amide; diisopropylamine; toluene; barium carbonate; In tetrahydrofuran; 1,4-dioxane; methanol; tetrachloromethane; water;

DOI:10.1016/S0040-4039(00)95922-7

upstream raw materials:

C₂₈H₃₆O₇

methyl 2,6-dideoxy-3-C-methyl-α-D-arabino-hexopyranoside

methyl 4,6-O-(R)-benzylidene-2-deoxy-α-D-erythrohexopyranosid-3-ulose

(2R,4aR,6S,8aS)-6-Methoxy-8-methylene-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine