(2R,3R,4R,6S)-3-((2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-methyl-3-phenylselanyl-tetrahydro-pyran-2-yloxy)-6-methoxy-2,4-dimethyl-tetrahydro-pyran-4-ol

Base Information

• Chemical Name: (2R,3R,4R,6S)-3-((2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-methyl-3-phenylselanyl-tetrahydro-pyran-2-yloxy)-6-methoxy-2,4-dimethyl-tetrahydro-pyran-4-ol
• CAS No.: 110906-71-3
• Molecular Formula: C₃₄H₄₂O₇Se
• Molecular Weight: 641.663

Synonyms:(2R,3R,4R,6S)-3-((2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-methyl-3-phenylselanyl-tetrahydro-pyran-2-yloxy)-6-methoxy-2,4-dimethyl-tetrahydro-pyran-4-ol

Chemical Property of (2R,3R,4R,6S)-3-((2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-methyl-3-phenylselanyl-tetrahydro-pyran-2-yloxy)-6-methoxy-2,4-dimethyl-tetrahydro-pyran-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,6S)-3-((2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-methyl-3-phenylselanyl-tetrahydro-pyran-2-yloxy)-6-methoxy-2,4-dimethyl-tetrahydro-pyran-4-ol

There total 11 articles about (2R,3R,4R,6S)-3-((2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-methyl-3-phenylselanyl-tetrahydro-pyran-2-yloxy)-6-methoxy-2,4-dimethyl-tetrahydro-pyran-4-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: 88.0%

Benzoic acid (2R,3R,4R,6S)-3-((2R,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-methyl-3-phenylselanyl-tetrahydro-pyran-2-yloxy)-6-methoxy-2,4-dimethyl-tetrahydro-pyran-4-yl ester (110906-70-2) → (2R,3R,4R,6S)-3-((2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-methyl-3-phenylselanyl-tetrahydro-pyran-2-yloxy)-6-methoxy-2,4-dimethyl-tetrahydro-pyran-4-ol (110906-71-3)

Guidance literature:

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) → (2R,3R,4R,6S)-3-((2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-methyl-3-phenylselanyl-tetrahydro-pyran-2-yloxy)-6-methoxy-2,4-dimethyl-tetrahydro-pyran-4-ol (110906-71-3)

Guidance literature:

Multi-step reaction with 7 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: 1.) Bu₃SnO 2.) Et₃N / 1.) PhCH₃, reflux, 4 h 2.) room temp. 1 h

6: 2.) sym-collidine / 2.) CH₃CN

7: 88 percent

With 2,4,6-trimethyl-pyridine; sodium tetrahydroborate; N-Bromosuccinimide; lithium aluminium tetrahydride; mercury(II) diacetate; sodium amide; triethylamine; barium carbonate; In tetrahydrofuran; tetrachloromethane;

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

Reference yield:

(2R,4aR,6S,8aS)-6-Methoxy-8-methylene-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine (72244-36-1) → (2R,3R,4R,6S)-3-((2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-methyl-3-phenylselanyl-tetrahydro-pyran-2-yloxy)-6-methoxy-2,4-dimethyl-tetrahydro-pyran-4-ol (110906-71-3)

Guidance literature:

Multi-step reaction with 6 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: 1.) Bu₃SnO 2.) Et₃N / 1.) PhCH₃, reflux, 4 h 2.) room temp. 1 h

5: 2.) sym-collidine / 2.) CH₃CN

6: 88 percent

With 2,4,6-trimethyl-pyridine; sodium tetrahydroborate; N-Bromosuccinimide; lithium aluminium tetrahydride; mercury(II) diacetate; triethylamine; barium carbonate; In tetrahydrofuran; tetrachloromethane;

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

upstream raw materials:

Benzoic acid (2R,3R,4R,6S)-3-((2R,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-methyl-3-phenylselanyl-tetrahydro-pyran-2-yloxy)-6-methoxy-2,4-dimethyl-tetrahydro-pyran-4-yl ester

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

Downstream raw materials:

C₃₄H₄₂O₈Se

(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

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

C₂₈H₃₆O₇

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