Benzoic acid (2R,3S,6R)-6-tert-butoxy-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: Benzoic acid (2R,3S,6R)-6-tert-butoxy-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 107123-48-8
• Molecular Formula: C₁₇H₂₄O₅
• Molecular Weight: 308.375

Synonyms:Benzoic acid (2R,3S,6R)-6-tert-butoxy-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester

Chemical Property of Benzoic acid (2R,3S,6R)-6-tert-butoxy-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

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Technology Process of Benzoic acid (2R,3S,6R)-6-tert-butoxy-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester

There total 4 articles about Benzoic acid (2R,3S,6R)-6-tert-butoxy-3-hydroxy-tetrahydro-pyran-2-ylmethyl 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:

tert-butyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside (69247-20-7,149279-18-5,23339-25-5) → Benzoic acid (2R,3S,6R)-6-tert-butoxy-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester (107123-48-8)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / Pd-C(5percent) / ethyl acetate / 12 h

2: Et₃N, H₂O / methanol / Ambient temperature

3: CH₂Cl₂ / 0 deg C, then room temp., overnight

With water; hydrogen; triethylamine; 5%-palladium/activated carbon; In methanol; dichloromethane; ethyl acetate;

DOI:10.1016/S0040-4020(01)90575-7

Reference yield:

D-glucal triacetate (2873-29-2) → Benzoic acid (2R,3S,6R)-6-tert-butoxy-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester (107123-48-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 97 percent / BF₃-Et₂O / 1.67 h / Ambient temperature

2: H₂ / Pd-C(5percent) / ethyl acetate / 12 h

3: Et₃N, H₂O / methanol / Ambient temperature

4: CH₂Cl₂ / 0 deg C, then room temp., overnight

With boron trifluoride diethyl etherate; water; hydrogen; triethylamine; 5%-palladium/activated carbon; In methanol; dichloromethane; ethyl acetate;

DOI:10.1016/S0040-4020(01)90575-7

Reference yield:

Acetic acid (2R,3S,6R)-2-acetoxymethyl-6-tert-butoxy-tetrahydro-pyran-3-yl ester (107108-66-7) → Benzoic acid (2R,3S,6R)-6-tert-butoxy-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester (107123-48-8)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N, H₂O / methanol / Ambient temperature

2: CH₂Cl₂ / 0 deg C, then room temp., overnight

With water; triethylamine; In methanol; dichloromethane;

DOI:10.1016/S0040-4020(01)90575-7

upstream raw materials:

benzoyl chloride

tert-butyl 2,3-deoxy-α-D-glucopyranoside

Acetic acid (2R,3S,6R)-2-acetoxymethyl-6-tert-butoxy-tetrahydro-pyran-3-yl ester

tert-butyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside

Downstream raw materials:

(2R,3S,6R)-2-((S)-2-Benzenesulfonyl-1-methyl-ethyl)-6-tert-butoxy-tetrahydro-pyran-3-ol

(2R,3S,6R)-2-((R)-2-Benzenesulfonyl-1-methyl-ethyl)-6-tert-butoxy-tetrahydro-pyran-3-ol

(2S,3S)-1-Benzenesulfonyl-6-[1,3]dithian-2-yl-2-methyl-hexan-3-ol

(2R,3S)-1-Benzenesulfonyl-6-[1,3]dithian-2-yl-2-methyl-hexan-3-ol

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